Pyridine derivatives as pesticides

ABSTRACT

Compounds of formu (I) wherein n and Z are as defined in claim 1, and, where appropriate, tautomers thereof, in each case in free form, or in salt form, can be used as agrochemical active ingredients and can be prepared in a manner known per se.

This is a 371 of PCT/EP94/04222 Dec. 19, 1994 now WO 95/18123 Jul. 6, 1995.

The invention relates to compounds of formula ##STR1## wherein, taking into account the proviso mentioned below, n is 0 or 1, and

Z is a 5- or 6-membered heterocyclyl which is bonded via a nitrogen atom that is part of the basic ring structure of the heterocyclyl radical to the nitrogen atom (shown in formula I) in the 3-substituent of the pyridine ring,

in free form or in salt form, where appropriate to tautomers, in free form or in salt form, of those compounds, to a process for the preparation of those compounds and tautomers and to the use of those compounds and tautomers, to pesticidal compositions the active ingredient of which is selected from those compounds and tautomers, in each case in free form or in agrochemically acceptable salt form, to a process for the preparation of those compositions and to the use of those compositions, to plant propagation material treated with those compositions, to a method of controlling pests, to intermediates, in free form or in salt form, for the preparation of those compounds, where appropriate to tautomers, in free form or in salt form, of those intermediates, and to a process for the preparation of those intermediates and their tautomers and to the use of those intermediates and their tautomers.

In the literature, certain pyridine derivatives are proposed as insecticidal active ingredients of pesticides. The biological properties of those known compounds are not entirely satisfactory in the field of pest control, however, and there is therefore a need to provide further compounds having pesticidal properties, especially for controlling insects and representatives of the order Acarina. That problem is solved according to the invention by the provision of the present compounds I.

As is familiar to a person skilled in the art, some compounds I may be in the form of tautomers. Accordingly, hereinbefore and hereinafter compounds I are to be understood as including corresponding tautomers, even though the latter are not specifically mentioned in each case.

Compounds I having at least one basic centre are capable of forming, for example, acid addition salts. Those salts are formed, for example, with strong inorganic acids, such as mineral acids, for example perchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphoric acid or a hydrohalic acid, with strong organic carboxylic acids, such as unsubstituted or substituted, for example halo-substituted, C₁ -C₄ alkanecarboxylic acids, for example acetic acid, or saturated or unsaturated dicarboxylic acids, for example oxalic, malonic, succinic, maleic, fumaric or phthalic acid, or hydroxycarboxylic acids, for example ascorbic, lactic, malic, tartaric or citric acid, or benzoic acid, or with organic sulfonic acids, such as unsubstituted or substituted, for example halo-substituted, C₁ -C₄ alkanesulfonic or arylsulfonic acids, for example methanesulfonic or p-toluene-sulfonic acid. Furthermore, compounds I having at least one acidic group are capable of forming salts with bases. Suitable salts with bases are, for example, metal salts, such as alkali metal or alkaline earth metal salts, for example sodium, potassium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower alkylamine, for example ethylamine, diethylamine, triethylamine or dimethylpropylamine, or a mono-, di- or tri-hydroxy-lower alkylamine, for example mono-, di- or tri-ethanolamine. Where appropriate, corresponding internal salts may also be formed. Preference is given within the scope of the invention to agrochemically advantageous salts, but salts that have disadvantages for agrochemical purposes, for example salts that are toxic to bees or to fish, are also included; the latter salts are used, for example, in the isolation or purification of free compounds I or the agrochemically acceptable salts thereof. In view of the close relationship between the compounds I in free form and in the form of their salts, hereinbefore and hereinafter any reference to the free compounds I or their salts should be understood as including also the corresponding salts or the free compounds I, respectively, where appropriate and expedient. The same applies to tautomers of compounds I and the salts thereof. The free form is generally preferred.

Preferred forms within the scope of the invention are:

(1) a compound of formula I wherein, taking into account the proviso mentioned below,

n is 0;

(2) a compound of formula I wherein, taking into account the proviso mentioned below,

Z is a radical of formula ##STR2## wherein m is 0 or 1, and

A, D, E, G and, when m is 1, B, are each independently of the others O, S, S(═O), S(═O)₂, unsubstituted or substituted C or unsubstituted or substituted N, and are each bonded via a single bond or a double bond to the two adjacent ring members to form a stable hetero-cyclic five-membered ring when m is 0 or a stable heterocyclic six-membered ring when m is 1;

(3) a compound of formula ##STR3## wherein A is CR₁ R₂, or, when B is neither O nor S, is --CR₃ ═;

B is CR₄ R₅, --CR₆ ═, O, S, NR₇ or --N═;

D is CR₁₃ R₁₄, --CR₁₅ ═, O, S, NR₁₆ or --N═;

E is NR₁₇ or, when D is not a hetero atom, is O or S; and

G is CO, CS, CNR₂₁ or CNOR₂₂ ;

R₇, R₁₆, R₁₇ and R₂₁ are each independently of the others H, C₁ -C₅ alkyl, C₁ -C₅ alkyl substituted by from 1 to 3 substituents from the group consisting of halogen, hydroxy, C₁ -C₃ alkoxy and C₁ -C₃ alkylthio; C₃ -C₆ cycloalkyl, C₃ -C₆ cycloalkyl substituted by from 1 to 3 substituents from the group consisting of halogen and C₁ -C₃ alkyl; COOR₈, CONR₉ R₁₀, COR₁₁, COSR₁₂, NR₁₈ R₁₉ or N═CR₂₀ ;

R₁ and R₂ are each independently of the other R₂₃ or together are ═O, ═NH or ═S;

R₄ and R₅ are each independently of the other R₂₃ or together are ═O, ═NH or ═S;

R₁₃ and R₁₄ are each independently of the other R₂₃ or together are ═O, ═NH or ═S;

R₃, R₆, R₈, R₉, R₁₀, R₁₁, R₁₂, R₁₅, R₁₈, R₁₉, R₂₂ and R₂₃ are each independent others H, halogen, C₁ -C₅ alkyl, C₁ -C₅ alkenyl, C₁ -C₅ alkoxy, C₁ -C₃ alkoxy-C₁ -C₅ alkyl, hydroxy-C₁ -C₅ alkyl, C₁ -C₅ alkoxycarbonyl, C₁ -C₅ alkylthio; C₁ -C₅ alkyl substituted by from 1 to 3 substituents from the group consisting of halogen, hydroxy, C₁ -C₃ alkoxy, C₁ -C₃ alkoxycarbonyl and C₁ -C₃ alkylthio; C₃ -C₆ cycloalkyl or C₃ -C₆ cycloalkyl substituted by from 1 to 3 substituents from the group consisting of halogen and C₁ -C₃ alkyl; and

R₂₀ is C₁ -C₅ alkyl, C₁ -C₅ alkyl substituted by from 1 to 3 substituents from the group consisting of halogen, hydroxy, C₁ -C₃ alkoxy and C₁ -C₃ alkylthio; C₃ -C₆ cycloalkyl, C₃ -C₆ cycloalkyl substituted by from 1 to 3 substituents from the group consisting of halogen and C₁ -C₃ alkyl; unsubstituted or substituted phenyl or unsubstituted or substituted pyridyl;

with the proviso that in compounds of formula I wherein Z is a radical of formula II and n is 0, G is other than CO when m is 1, D is --N═, R₁ is H, C₁ -C₅ alkyl or C₃ -C₆ cycloalkyl, R₂ is H or C₁ -C₆ alkyl, R₆ is H, C₁ -C₅ alkyl, C₃ -C₆ cycloalkyl, C₁ -C₃ alkoxy-C₁ -C₅ alkyl or halo-C₁ -C₂ alkyl, and R₁₇ is H; and with the further proviso that in compounds of formula I wherein Z is a radical of formula II and n is 1, G is other than CO when m is 1, D is --N═, R₁ and R₂ are each independently of the other H or C₁ -C₅ alkyl, R₆ is C₁ -C₅ alkyl or C₃ -C₆ cycloalkyl, and R₁₇ is H;

and with the further proviso that in compounds of formula I wherein Z is a radical of formula II, G is other than CO when m is 0, D is --CR₁₅ ═, R₃ and R₁₅ are each independently of the other H, C₁ -C₅ alkyl, C₁ -C₅ alkyl substituted by from 1 to 3 substituents from the group consisting of halogen, hydroxy, C₁ -C₃ alkoxy and C₁ -C₃ alkylthio; C₃ -C₆ cycloalkyl or C₃ -C₆ cycloalkyl substituted by from 1 to 3 substituents from the group consisting of halogen and C₁ -C₃ alkyl; and R₁₇ is H. C₁ -C₅ alkyl, C₁ -C₅ alkyl substituted by from 1 to 3 substituents from the group consisting of halogen, hydroxy, C₁ -C₃ alkoxy and C₁ -C₃ alkylthio; C₃ -C₆ cycloalkyl, C₃ -C₆ cycloalkyl substituted by from 1 to 3 substituents from the group consisting of halogen and C₁ -C₃ alkyl; COOR₈, CONR₉ R₁₀, COR₁₁, COSR₁₂, NR₁₈ R₁₉ or N═CR₂₀ ;

(4) a compound of formula III wherein, taking into account the proviso mentioned above, B, when m is 1, is CR₄ R₅, --CR₆ ═, O, NR₇ or --N═, preferably CR₄ R₅ or --CR₆ ═, especially CR₄ R₅ ;

(5) a compound of formula III wherein, taking into account the proviso mentioned above, D is CR₁₃ R₁₄, --CR₁₅ ═, NR₁₆ or --N═, preferably CR₁₃ R₁₄, --CR₁₅ ═ or --N═, especially CR₁₃ R₁₄ or --N═;

(6) a compound of formula III wherein, taking into account the proviso mentioned above, E is NR₁₇ ;

(7) a compound of formula III wherein, taking into account the proviso mentioned above, G is CO, CS or CNR₂₁, preferably CO or CS, especially CO;

(8) a compound of formula III wherein, taking into account the proviso mentioned above, R₁ and R₂ are each independently of the other H, C₁ -C₅ alkyl, C₁ -C₅ alkyl substituted by from 1 to 3 substituents from the group consisting of halogen and C₁ -C₃ alkoxy, or C₃ -C₆ cycloalkyl, preferably H, C_(1-C) ₄ alkyl or C₃ -C₆ cycloalkyl, especially H or C₁ -C₄ alkyl;

(9) a compound of formula III wherein, taking into account the proviso mentioned above, R₁ and R₂ together are ═O or ═S, preferably ═O;

(10) a compound of formula III wherein, taking into account the proviso mentioned above, R₃ is H, halogen, C₁ -C₃ alkyl, C₁ -C₃ alkylthio, C₁ -C₃ alkyl substituted by from 1 to 3 substituents from the group consisting of halogen, hydroxy, C₁ -C₂ alkoxy and C₁ -C₂ alkylthio, or C₃ -C₆ cycloalkyl, preferably H, C₁ -C₃ alkyl, C₁ -C₂ alkyl substituted by from 1 to 3 substituents from the group consisting of halogen, hydroxy and C₁ -C₂ alkoxy, or C₃ -C₆ cycloalkyl, especially H, C₁ -C₃ alkyl, C₁ -C₂ alkyl or C₃ -C₆ cycloalkyl;

(11) a compound of formula III wherein, taking into account the proviso mentioned above, R₄ and R₅ are each independently of the other H, C₁ -C₃ alkyl, C₁ -C₃ alkoxy, C₁ -C₃ alkyl substituted by from 1 to 3 substituents from the group consisting of halogen, hydroxy, C₁ -C₃ alkoxy and C₁ -C₃ alkylthio, or C₃ -C₆ cycloalkyl, preferably H, C₁ -C₃ alkyl, C₁ -C₃ alkoxy or C₃ -C₆ cycloalkyl, especially H, C₁ -C₃ alkyl or C₁ -C₃ alkoxy;

(12) a compound of formula III wherein, taking into account the proviso mentioned above, R₄ and R₅ together are ═O or ═S, preferably ═O;

(13) a compound of formula III wherein, taking into account the proviso mentioned above, R₆ is H, C₁ -C₅ alkyl, C₁ -C₅ alkoxy or C₃ -C₆ cycloalkyl, preferably H, C₁ -C₄ alkyl or C₃ -C₆ cycloalkyl, especially H or C₁ -C₃ alkyl;

(14) a compound of formula III wherein, taking into account the proviso mentioned above, R₇ is H, C₁ -C₃ alkyl, C₁ -C₃ alkyl substituted by from 1 to 3 substituents from the group consisting of halogen and C₁ -C₃ alkoxy; C₃ -C₆ cycloalkyl, COOR₈, CONR₉ R₁₀ or COR₁₁, preferably H, C₁ -C₃ alkyl, C₁ -C₃ alkyl substituted by from 1 to 3 substituents from the group halogen; CONR₉ R₁₀ or COR₁₁, especially H, C₁ -C₃ alkyl or COR₁₁ ;

(15) a compound of formula III wherein, taking into account the proviso mentioned above, R₈ is C₁ -C₅ alkyl, C₁ -C₅ alkyl substituted by from 1 to 3 substituents from the group consisting of halogen, hydroxy, C₁ -C₃ alkoxy and C₁ -C₃ alkylthio, or C₃ -C₆ cycloalkyl, preferably C₁ -C₄ alkyl or C₃ -C₆ cycloalkyl, especially C₁ -C₃ alkyl;

(16) a compound of formula III wherein, taking into account the proviso mentioned above, R₉ and R₁₀ are each independently of the other H, C₁ -C₅ alkyl, C₁ -C₅ alkyl substituted by from 1 to 3 substituents from the group consisting of halogen, hydroxy, C₁ -C₃ alkoxy and C₁ -C₃ alkylthio, or C₃ -C₆ cycloalkyl, preferably H, C₁ -C₄ alkyl or C₃ -C₆ cycloalkyl, especially H or C₁ -C₃ alkyl;

(17) a compound of formula III wherein, taking into account the proviso mentioned above, R₁₁ is C₁ -C₅ alkyl, C₁ -C₅ alkyl substituted by from 1 to 3 substituents from the group consisting of halogen, hydroxy, C₁ -C₃ alkoxy and C₁ -C₃ alkylthio, or C₃ -C₆ cycloalkyl, preferably C₁ -C₄ alkyl, C₁ -C₄ alkyl substituted by from 1 to 3 substituents from the group consisting of halogen and C₁ -C₃ alkoxy, or C₃ -C₆ cycloalkyl, especially C₁ -C₄ alkyl;

(18) a compound of formula III wherein, taking into account the proviso mentioned above, R₁₂ is C₁₄ -C₅ alkyl;

(19) a compound of formula III wherein, taking into account the proviso mentioned above, R₁₃ and R₁₄ are each independently of the other H, C₁ -C₅ alkyl, C₁ -C₅ alkenyl, C₁ -C₅ alkyl substituted by from 1 to 3 substituents from the group consisting of halogen, hydroxy, C₁ -C₃ alkoxy, C₁ -C₃ alkoxycarbonyl and C₁ -C₃ alkylthio, or C₃ -C₆ cycloalkyl, preferably H, C₁ -C₅ alkyl or C₃ -C₆ cycloalkyl, especially H or C₁ -C₃ alkyl;

(20) a compound of formula III wherein, taking into account the proviso mentioned above, R₁₃ and R₁₄ together are ═O;

(21) a compound of formula III wherein, taking into account the proviso mentioned above, R₁₅ is H, C₁ -C₅ alkyl, C₁ -C₅ alkoxycarbonyl or C₃ -C₆ cycloalkyl, preferably H, C₁ -C₃ alkyl or C₃ -C₆ cycloalkyl, especially H or C₁ -C₃ alkyl;

(22) a compound of formula III wherein, taking into account the proviso mentioned above, R₁₆ is H, C₁ -C₅ alkyl, C₃ -C₆ cycloalkyl, COOR₈, CONR₉ R₁₀ or COR₁₁, preferably H, C₁ -C₅ alkyl or COR₁₁, especially H or COR₁₁ ;

(23) a compound of formula III wherein, taking into account the proviso mentioned above, R₁₇ is H, C₁ -C₅ alkyl, C₁ -C₅ alkyl substituted by from 1 to 3 substituents from the group halogen, or C₃ -C₆ cycloalkyl, COOR₈, CONR₉ R₁₀, COR₁₁ or N═CR₂₀, preferably H, C₁ -C₅ alkyl, CONR₉ R₁₀, COR₁₁ or N═CR₂₀, especially H, C₁ -C₃ alkyl or COR₁₁ ;

(24) a compound of formula III wherein, taking into account the proviso mentioned above, R₁₈ and R₁₉ are each independently of the other H, C₁ -C₅ alkyl or C₃ -C₆ cycloalkyl, Preferably H or C₁ -C₅ alkyl, especially C₁ -C₃ alkyl;

(25) a compound of formula III wherein, taking into account the proviso mentioned above, R₂₀ is C₁ -C₅ alkyl, C₃ -C₆ cycloalkyl, unsubstituted or substituted phenyl or unsubstituted or substituted pyridyl, preferably unsubstituted or substituted phenyl or unsubstituted or substituted pyridyl, especially unsubstituted o r substituted pyridyl;

(26) a compound of formula III wherein, taking into account the proviso mentioned above, R₂₁ is H or C₁ -C₅ alkyl, preferably H;

(27) a compound of formula III wherein, taking into account the proviso mentioned above, R₂₂ is C₁ -C₅ alkyl, preferably C₁ -C₂ alkyl;

(28) a compound of formula III wherein, taking into account the proviso mentioned above,

n is 0,

B, when m is 1, is CR₄ R₅, --CR₆ ═, O, NR₇ or --N═,

D is CR₁₃ R₁₄, --CR₁₅ ═, NR₁₆ or --N═,

E is NR₁₇,

G is CO, CS or CNR₂₁,

R₁ and R₂ are each independently of the other H, C₁ -C₅ alkyl, C₁ -C₅ alkyl substituted by from 1 to 3 substituents from the group consisting of halogen and C₁ -C₃ alkoxy, or C₃ -C₆ Cycloalkyl, or together are ═O or ═S,

R₃ is H, halogen, C₁ -C₃ alkyl, C₁ -C₃ alkylthio, C₁ -C₃ alkyl substituted by from 1 to 3 substituents from the group consisting of halogen, hydroxy, C₁ -C₂ alkoxy and C₁ -C₂ alkylthio, or C₃ -C₆ cycloalkyl,

R₄ and R₅ are each independently of the other H, C₁ -C₃ alkyl, C₁ -C₃ alkoxy, C₁ -C₃ alkyl substituted by from 1 to 3 substituents from the group consisting of halogen, hydroxy, C₁ -C₃ alkoxy and C₁ -C₃ alkylthio, or C₃ -C₆ cycloalkyl, or together are ═O or ═S,

R₆ is H, C₁ -C₅ alkyl, C₁ -C₅ alkoxy or C₃ -C₆ cycloalkyl,

R₇ is H, C₁ -C₃ alkyl, C₁ -C₃ alkyl substituted by from 1 to 3 substituents from the group consisting of halogen and C₁ -C₃ alkoxy, C₃ -C₆ cycloalkyl, COOR₈, CONR₉ R₁₀ or COR₁₁,

R₈ is C₁ -C₅ alkyl, C₁ -C₅ alkyl substituted by from 1 to 3 substituents from the group consisting of halogen, hydroxy, C₁ -C₃ alkoxy and C₁ -C₃ alkylthio, or C₃ -C₆ cycloalkyl,

R₉ and R₁₀ are each independently of the other H, C₁ -C₅ alkyl, C₁ -C₅ alkyl substituted by from 1 to 3 substituents from the group consisting of halogen, hydroxy, C₁ -C₃ alkoxy and C₁ -C₃ alkylthio, or C₃ -C₆ cycloalkyl,

R₁₁ is C₁ -C₅ alkyl, C₁ -C₅ alkyl substituted by from 1 to 3 substituents from the group consisting of halogen, hydroxy, C₁ -C₃ alkoxy and C₁ -C₃ alkylthio, or C₃ -C₆ cycloalkyl,

R₁₃ and R₁₄ are each independently of the other H, C₁ -C₅ alkyl, C₁ -C₅ alkenyl, C₁ -C₅ alkyl substituted by from 1 to 3 substituents from the group consisting of halogen, hydroxy, C₁ -C₃ alkoxy, C₁ -C₃ alkoxycarbonyl and C₁ -C₃ alkylthio, or C₃ -C₆ cycloalkyl, or together are ═O,

R₁₅ is H, C₁ -C₅ alkyl, C₁ -C₅ alkoxycarbonyl or C₃ -C₆ cycloalkyl,

R₁₆ is H, C₁ -C₅ alkyl, C₃ -C₆ cycloalkyl, COOR₈, CONR₉ R₁₀ or COR₁₁, R₁₇ H, C₁ -C₅ alkyl, C₁ -C₅ alkyl substituted by from 1 to 3 substituents from the group halogen, or C₃ -C₆ cycloalkyl, COOR₈, CONR₉ R₁₀, COR₁₁ or N═CR₂₀,

R₂₀ is C₁ -C₅ alkyl, C₃ -C₆ cycloalkyl, unsubstituted or substituted phenyl or unsubstituted or substituted pyridyl, and

R₂₁ is H or C₁ -C₅ alkyl;

(29) a compound of formula III wherein, taking into account the proviso mentioned above,

n is0,

B, when m is 1, is CR₄ R₅ or --CR₆ ═,

D is CR₁₃ R₁₄, --CR₁₅ ═ or --N═,

E is NR₁₇,

G is CO or CS,

R₁ and R₂ are each independently of the other H, C₁ -C₄ alkyl, or C₃ -C₆ cycloalkyl, or together are ═O or ═S,

R₃ is H, C₁ -C₃ alkyl, C₁ -C₂ alkyl substituted by from 1 to 3 substituents from the group consisting of halogen, hydroxy and C₁ -C₂ alkoxy, or C₃ -C₆ cycloalkyl,

R₄ and R₅ are each independently of the other H, C_(1-C) ₃ alkyl, C₁ -C₃ alkoxy or C₃ -C₆ cycloalkyl, or together are ═O or ═S,

R₆ is H, C₁ -C₄ alkyl or C₃ -C₆ cycloalkyl,

R₁₃ and R₁₄ are each independently of the other H, C₁ -C₅ alkyl or C₃ -C₆ cycloalkyl, or together are ═O,

R₁₅ is H, C₁ -C₃ alkyl or C₃ -C₆ cycloalkyl,

R₁₇ is H, C₁ -C₅ alkyl, CONR₉ R₁₀, COR₁₁ or N═CR₂₀, and

R₂₀ is unsubstituted or substituted phenyl or unsubstituted or substituted pyridyl;

(30) a compound of formula III wherein, taking into account the proviso mentioned above,

n is 0,

B, when m is 1, is CR₄ R₅,

D is C₁₃ R₁₄ or --N═,

E is NR₁₇,

G is CO,

R₁ and R₂ are each independently of the other H or C₁ -C₄ alkyl, or together are ═O,

R₃ is H, C₁ -C₃ alkyl, C₁ -C₂ alkyl or C₃ -C₆ cycloalkyl,

R₄ and R₅ are each independently of the other H, C₁ -C₃ alkyl or C₁ -C₃ alkoxy, or together are ═O,

R₁₃ and R₁₄ are each independently of the other H or C₁ -C₃ alkyl, or together are ═O, and

R₁₇ is H, C₁ -C₃ alkyl, or COR₁₁ ;

in each case in free form or in salt form, and where appropriate a tautomer, in free form or in salt form, of that compound.

Special preference is given within the scope of the invention to the compounds of formula I given in Examples P1 to P9.

Within the scope of the invention preference is given specifically to the compounds of formula I wherein

n is 0 and Z is 4-methyl-2-oxo-perhydroimidazol-1-yl, and

n is 1 and Z is 6-ethoxymethyl-4,5-dihydro-2H 1,2,4!triazin-3-on-4-yl.

Unless otherwise defined, the general terms used hereinbefore and hereinafter have the meanings given below.

Halogen--as a group per se and as a structural unit of other groups and compounds, such as haloalkyl and halocycloalkyl--is fluorine, chlorine, bromine or iodine, especially fluorine, chlorine or bromine, more especially fluorine or chlorine.

Unless otherwise defined, carbon-containing groups and compounds each contain from 1 up to and including 6, preferably from 1 up to and including 4, especially 1 or 2, carbon atoms.

C₃ -C₆ cycloalkyl--as a group per se and as a structural unit of other groups and compounds, such as halocycloalkyl--is cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

Alkyl--as a group per se and as a structural unit of other groups and compounds, such as haloalkyl, alkoxy and alkylthio--is, in each case duly taking into account the number of carbon atoms present in the group or compound in question, either straight-chained, for example methyl, ethyl, propyl or butyl, or branched, for example isopropyl, isobutyl, secbutyl, tert-butyl, isopentyl or neopentyl.

Halo-substituted carbon-containing groups and compounds, such as haloalkyl or halocycloalkyl, may be partially halogenated or perhalogenated, it being possible in the case of multiple halogenation for the halogen substituents to be identical or different Examples of haloalkyl--as a group per se and as a structural unit of other groups and compounds, such as haloalkylthio--are methyl mono- to tri-substituted by fluorine, chlorine and/or by bromine, such as CHF₂ or CF₃ ; ethyl mono- to penta-substituted by fluorine, chlorine and/or by bromine, such as CH₂ CF₃, CF₂ CF₃, CF₂ CCI₃, CF₂ CHCl₂, CF₂ CHF₂, CF₂ CFCL₂, CF₂ CHBr₂, CF₂ CHCIF, CF₂ CHBrF or CClFCHClF; propyl or isopropyl mono- to heptasubstituted by fluorine, chlorine and/or by bromine, such as CH₂ CHBrCH₂ Br, CF₂ CHFCF₃, CH₂ CF₂ CF₃ or CH(CF₃)₂ ; butyl mono- to nona-substituted by fluorine, chlorine and/or by bromine, or one of the isomers thereof, such as CF(CF₃)CHFCF₃ or CH₂ (CF₂)₂ CF₃ ; and pentyl mono- to undeca-substituted by fluorine, chlorine and/or by bromine, or one of the isomers thereof, such as CF(CF₃)CHCH₂ FCF₃ or CH₂ CH₂ CH₂ CH₂ CH₂ Cl.

The invention relates also to a process for the preparation of the compounds of formula I or, where appropriate, the tautomers thereof, in each case in free form or in salt form, taking into account the proviso mentioned above, which process comprises, for example

a) for the preparation of a compound of formula I wherein n is 0, reacting a compound of formula

    Z--NH.sub.2                                                (IV),

which is known or which can be prepared analogously to corresponding known compounds and wherein Z is as defined for formula I, preferably in the presence of an acid, with pyridine-3-carbaldehyde, or

b) for the preparation of a compound of formula I wherein n is 1, reacting a compound of formula IV, preferably in the presence of an acid, with N-oxidopyridinio-3-carbaldehyde or N-oxidopyridinio-3-carbaldehyde dimethylacetal, which are known, or

c) for the preparation of a compound of formula I wherein Z is a radical of formula II and wherein n is 0, G is CO and E is NH, heating a compound of formula ##STR4## which is known or can be prepared analogously to corresponding known compounds and wherein A, B, D and m are as defined for formula I and Y is N, preferably in the presence of a base, or

d) for the preparation of a compound of formula I wherein Z is a radical of formula II and wherein n is 0, G is CO and E is NR₁₇, R₁₇ being other than H, reacting a compound of formula I wherein n is 0, G is CO and E is NH, preferably in the presence of a base, with a compound of formula R₁₇ COX₁ wherein X₁ is a leaving group, preferably halogen, especially chlorine, and in each case, if desired, converting a compound of formula I obtainable according to the process or by a different method, or a tautomer thereof, in each case in free form or in salt form, into a different compound of formula I or a tautomer thereof, for example converting a compound of formula I wherein n is 0 into a compound of formula I wherein n is 1, separating a mixture of isomers obtainable according to the process and isolating the desired isomer and/or converting a free compound of formula I obtainable according to the process or a tautomer thereof into a salt or converting a salt of a compound of formula I obtainable according to the process or a tautomer thereof into the free compound of formula I or a tautomer thereof or into a different salt.

The invention relates also to a process for the preparation of the compounds of formula IV, in each case in free form or in salt form, which process comprises, for example,

e) for the preparation of a compound of formula IV wherein Z is a radical of formula II and wherein G is CO, D is CR₁₅ and E is NR₁₇, reacting a compound of formula ##STR5## which is known or can be prepared analogously to corresponding known compounds and wherein A, B, R₁₅ and m are as defined for formula III and R₀ is a C₁ -C₆ alkyl group, with a compound of formula R₁₇ NH₂ wherein R₁₇ is as defined for formula III and then hydrolysing the resulting product, preferably in the presence of an acid, or

f) for the preparation of a compound of formula IV wherein Z is a radical of formula II and wherein A is --CR₃ ═, D is --N═, E is NH, G is CO and m is 0, reacting a compound of the formula CO(NHNH₂)₂, which is known or which can be prepared analogously to corresponding known compounds, with a compound of the formula R₃ C(OR)₃, which is known or can be prepared analogously to corresponding known compounds, and wherein R is a C₁ -C₆ alkyl group, or

g) for the preparation of a compound of formula IV wherein Z is a radical of formula II and wherein E is NH and G is CO, reacting a compound of formula ##STR6## which is known or which can be prepared analogously to corresponding known compounds and wherein A, B, D and m are as defined for formula III and Ar is unsubstituted or substituted phenyl or pyridyl, with hydrazine, or

h) for the preparation of a compound of formula IV wherein Z is a radical of formula II and wherein A is --CR₃ ═, D is --CR₁₅ ═, E is NH, G is CO and m is 0, hydrolysing a compound of formula ##STR7## which is known or can be prepared analogously to corresponding known compounds and wherein R₃ and R₁₅ are as defined for formula III and R is a C₁ -C₆ alkyl group, preferably in the presence of an acid, or

i) for the preparation of a compound of formula IV wherein Z is a radical of formula II and wherein A is CR₁ R₂, B is --CHR₆ ═, m is 1, D is --N═, E is NH and G is CO, hydrolysing a compound of formula ##STR8## which is novel and wherein R₁, R₂ and R₆ are as defined for formula III and R is a C₁ -C₆ alkyl group, preferably in the presence of an acid, or

j) for the preparation of a compound of formula IV wherein Z is a radical of formula II and wherein A is CR₁ R₂, B is CHR₄, m is 1, D and E are NH, and G is CO, hydrogenating a compound of formula ##STR9## which is known or can be prepared analogously to corresponding known compounds and wherein R₁, R₂ and R₆ are as defined for formula III, preferably in the presence of a reduction catalyst or a hydrogenating agent, and in each case, if desired, converting a compound of formula VI obtainable according to the process or by a different method, or a tautomer thereof, in each case in free form or in salt form, into a different compound of formula VI or a tautomer thereof, and/or separating a mixture of isomers obtainable according to the process and isolating the desired isomer.

The invention relates also to a process for the preparation of the compounds of formula V, in each case in free form or in salt from, which process comprises, for example

k) for the preparation of a compound of formula V wherein A is as defined for formula III, and B, when m is 1, is CR₄ R₅ or --CR₆ ═, and D is CHR₁₃ or --CR₁₅ ═, and Y is CH or N, reacting a compound of formula ##STR10## which is known or can be prepared analogously to corresponding known compounds and wherein Y is CH or N, preferably in the presence of an acid with a compound of formula ##STR11## which is known or can be prepared analogously to corresponding known compounds and wherein R₄, R₅ and R₁₃ are as defined for formula III, B, when m is 1, is CR₄ R₅ or --CR₆ ═, and X₂ is a leaving group, preferably halogen, especially chlorine, or with a compound of formula ##STR12## which is known or can be prepared analogously to corresponding known compounds and wherein R₄, R₅, R₁₃ and X₂ are as defined for formula XII and B, when m is 1, is CR₄ R₅ or --CR₆ ═, and R' and R" are each independently of the other C₁ -C₆ alkyl or together are --(CH₂)_(p) --, wherein p is 2 or 3, or with a compound of formula ##STR13## which is known or can be prepared analogously to corresponding known compounds and wherein R₄, R₅, R₁₃ and X₂ are as defined for formula XII, m is 1 and B is --CR₆ ═, and in each case, if desired, converting a compound of formula V obtainable according to the process or by a different method, or a tautomer thereof, in each case in free form or in salt form, into a different compound of formula V or a tautomer thereof, and/or separating a mixture of isomers obtainable according to the process and isolating the desired isomer.

The invention relates also to a process for the preparation of the compounds of formula VII, in each case in free form or in salt form, which process comprises, for example

l) heating a compound of formula V, preferably in the presence of a base, and in each case, if desired, converting a compound of formula VII obtainable according to the process or by a different method, or a tautomer thereof, in each case in free form or in salt form, into a different compound of formula VII or a tautomer thereof, and/or separating a mixture of isomers obtainable according to the process and isolating the desired isomer.

The invention relates also to a process for the preparation of the compounds of formula VIII, in each case in free form or in salt form, which process comprises, for example

m) reacting a compound of formula ##STR14## which is novel and wherein R, R₃ and R₁₅ are as defined for formula VIII, with ammonia and, if desired, converting a compound of formula VIII obtainable according to the process or by a different method, or a tautomer thereof, in each case in free form or in salt form, into a different compound of formula VIII or a tautomer thereof, and/or separating a mixture of isomers obtainable according to the process and isolating the desired isomer.

The compounds of formula IX wherein R₁, R₂ and R₆ are as defined for formula III and R is a C₁ -C₆ alkyl group are novel and the invention relates also thereto.

The invention relates also to a process for the preparation of the compounds of formula IX, in each case in free form or in salt form, which process comprises, for example

n) rearranging a compound of formula ##STR15## which is novel and wherein R₁, R₂ and R₆ are as defined for formula III and R'" and R"" are each independently of the other C₁ -C₆ alkyl, preferably methyl, or R'" is C₁ -C₆ alkyl and R"" is C₁ -C₅ alkoxy, preferably in the presence of an acid or a base, and in each case, if desired, converting a compound of formula IX obtainable according to the process or by a different method, or a tautomer thereof, in each case in free form or in salt form, into a different compound of formula IX or a tautomer thereof, and/or separating a mixture of isomers obtainable according to the process and isolating the desired isomer.

The compounds of formula XV wherein R, R₃ and R₁₅ are as defined for formula VIII are novel and the invention relates also thereto.

The invention relates also to a process for the preparation of the compounds of formula XI, in each case in free form or in salt form, which process comprises, for example

o) reacting a compound of formula ##STR16## which is known or can be prepared analogously to corresponding known compounds, with a compound of the formula X₃ CH(R₃)COR₁₅, which is known or can be prepared analogously to corresponding known compounds and wherein R, R₃ and R₁₅ are as defined for formula VIII and X₃ is a leaving group, for example halogen, preferably chlorine, preferably in the presence of a base,

and in each case, if desired, converting a compound of formula XV obtainable according to the process or by a different method, or a tautomer thereof, in each case in free form or in salt form, into a different compound of formula XV or a tautomer thereof, and/or separating a mixture of isomers obtainable according to the process and isolating the desired isomer.

The compounds of formula XVI wherein R₁, R₂ and R₆ are as defined for formula III and R'" and R'" are each independently of the other a C₁ -C₆ alkyl group, or R'" is a C₁ -C₆ alkyl group and R"" is a C₁ -C₅ alkoxy group, are novel and the invention relates also thereto.

The invention relates also to a process for the preparation of the compounds of formula XVI, in each case in free form or in salt form, which process comprises, for example

p) reacting a compound of formula ##STR17## wherein R'", R₁, R₂ and R₆ are as defined for formula XVI, with a compound of the formula NH₂ NHCOR', which is known or can be prepared analogously to corresponding known compounds and wherein R' is as defined for formula XVI, preferably in the presence of an acid,

and in each case, if desired, converting a compound of formula XVI obtainable according to the process or by a different method, or a tautomer thereof, in each case in free form or in salt form, into a different compound of formula XVI or a tautomer thereof, and/or separating a mixture of isomers obtainable according to the process and isolating the desired isomer.

The compounds of formula XVIII wherein R₁, R₂ and R₆ are as defined for formula III and R'" is a C₁ -C₆ alkyl group are novel and the invention relates also thereto.

The invention relates also to a process for the preparation of the compounds of formula XVIII, in each case in free from or in salt form, which process comprises, for example

q) reacting a compound of formula XVII with a compound of the formula R₆ COCR₁ R₂ X, which is known or can be prepared analogously to corresponding known compounds and wherein R₁, R₂ and R₆ are as defined for formula III and X is a leaving group, for example halogen, preferably chlorine, preferably in the presence of a base,

and in each case, if desired, converting a compound of formula XVIII obtainable according to the process or by a different method, or a tautomer thereof, in each case in free form or in salt form, into a different compound of formula XVIII or a tautomer thereof, and/or separating a mixture of isomers obtainable according to the process and isolating the desired isomer.

The remarks made above in relation to tautomers and/or salts of compounds I apply analogously to the starting materials listed hereinbefore and hereinafter as regards the tautomers and/or salts thereof.

The reactions described hereinbefore and hereinafter are carried out in a manner known per se, for example in the absence or, customarily, in the presence of a suitable solvent or diluent or of a mixture thereof, the reactions being carried out as required with cooling, at room temperature or with heating, for example in a temperature range from approximately -80° C. to the boiling temperature of the reaction medium, preferably from approximately -20° C. to approximately +150° C, and, if necessary, in a closed vessel, under pressure, in an inert gas atmosphere and/or under anhydrous conditions. Especially advantageous reaction conditions can be found in the Examples.

The starting materials given hereinbefore and hereinafter that are used for the preparation of compounds I, and where appropriate the tautomers thereof, in each case in free form or in salt form, are known or can be prepared in accordance with methods known per se, for example in accordance with the instructions given below.

Variant a):

Suitable acid catalysts for facilitating the reaction are, for example, those acids, used in catalytic amounts, that are listed above as suitable for the formation of acid addition salts with compounds I.

The reactants can be reacted with one another as such, i.e. without the addition of a solvent or diluent, for example in the melt In most cases, however, the addition of an inert solvent or diluent or of a mixture thereof is advantageous. Examples of such solvents or diluents that may be mentioned are: aromatic, aliphatic and alicyclic hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylene, mesitylene, tetralin, chlorobenzene, dichlorobenzene, bromobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, trichloromethane, tetrachloromethane, dichloroethane, trichloroethene or tetrachloroethene; esters, such as ethyl acetate; ethers, such as diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, tert-butyl methyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, dimethoxydiethyl ether, tetrahydrofuran or dioxane; ketones, such as acetone, methyl ethyl ketone or methyl isobutyl ketone; alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, ethylene glycol or glycerol; amides, such as N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone or hexamethylphosphoric acid triamide; nitriles, such as acetonitrile or propionitrile; and sulfoxides, such as dimethyl sulfoxide. If the reaction is carried out in the presence of a base, bases used in excess, such as triethylamine, pyridine, N-methylmorpholine or N,N-diethylaniline, may also serve as solvents or diluents. If the reaction is carried out in the presence of an acid catalyst, acids used in excess, for example strong organic carboxylic acids, such as unsubstituted or substituted, for example halo-substituted, C₁ -C₄ alkanecarboxylic acids, for example formic, acetic or propionic acid, may also serve as solvents or diluents.

The reaction is advantageously carried out in a temperature range from approximately 0° C. to approximately +100° C., preferably from approximately 20° C. to approximately +80° C.

In a preferred form of Variant a), the compound IV is reacted in an alcohol, preferably ethanol, in the presence of a mineral acid, preferably hydrochloric acid, at from 60° to 800°, preferably 80°, with pyridine-3-carbaldehyde.

Variant b):

Suitable acid catalysts for facilitating the reaction are, for example, acids of the type indicated in Variant a).

The reactants can be reacted with one another as such, i.e. without the addition of a solvent or diluent, for example in the melt. In most cases, however, the addition of an inert solvent or diluent or of a mixture thereof is advantageous. Examples of such solvents or diluents are, for example, those of the type mentioned under Variant a).

The reaction is advantageously carried out in a temperature range of from approximately 0° C. to approximately +100° C., preferably from approximately 20° C. to approximately +80° C.

Variant c):

Suitable bases for facilitating the reaction are, for example, alkali metal or alkaline earth metal hydroxides, hydrides, amides, alkanolates, acetates, carbonates, dialkylamides or alkylsilylamides, or alkylamines, alkylenediamines, unsubstituted or N-alkylated, saturated or unsaturated cycloalkylamines, basic heterocycles, ammonium hydroxides and carbocyclic amines. The following may be mentioned by way of example: sodium hydroxide, hydride, amide, methanolate, acetate or carbonate, potassium tert-butanolate, hydroxide, carbonate or hydride, lithium diisopropylamide, potassium bis(trimethylsilyl)amide, calcium hydride, triethylamine, diisopropylethylamine, triethylenediamine, cyclohexylamine, N-cyclohexyl-N,N-dimethylamine, N,N-diethylaniline, pyridine, 4-(N,N-dimethylamino)pyridine, quinuclidine, N-methylmorpholine, benzyl-trimethylammonium hydroxide and 1,5-diazabicyclo 5.4.0!undec-5-ene (DBU).

The reactants can be reacted with one another as such, i.e. without the addition of a solvent or diluent, for example in the melt. In most cases, however, the addition of an inert solvent or diluent or of a mixture thereof is advantageous. Examples of such solvents or diluents that may be mentioned are: aromatic, aliphatic and alicyclic hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylene, mesitylene, tetralin, chlorobenzene, dichlorobenzene, bromobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, trichloromethane, tetrachloromethane, dichloroethane, trichloroethene or tetrachloroethene; ethers, such as diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, tert-butyl methyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, dimethoxydiethyl ether, tetrahydrofuran or dioxane; ketones, such as acetone, methyl ethyl ketone or methyl isobutyl ketone; alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, ethylene glycol or glycerol; amides, such as N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone or hexamethylphosphoric acid triamide; nitriles, such as acetonitrile or propionitrile; and sulfoxides, such as dimethyl sulfoxide. If the reaction is carried out in the presence of a base, bases used in excess, such as triethylamine, pyridine, N-methylmorpholine or N,N-diethylaniline, may also serve as solvents or diluents.

The reaction is advantageously carried out in a temperature range from approximately 0° C. to approximately +100° C., preferably from approximately 20° C. to approximately +80° C.

Variant d):

Suitable bases for facilitating the reaction are, for example, those of the type mentioned under Variant c).

The reactants can be reacted with one another as such, i.e. without the addition of a solvent or diluent, for example in the melt. In most cases, however, the addition of an inert solvent or diluent or of a mixture thereof is advantageous. Examples of such solvents or diluents are, for example, those of the type mentioned under Variant c).

The reaction is advantageously carried out in a temperature range from approximately 0° C. to approximately +100° C., preferably from approximately 20° C. to approximately +80° C.

Variant e):

Suitable acid catalysts for facilitating the reaction are, for example, acids of the type mentioned under Variant a).

The reactants can be reacted with one another as such, i.e. without the addition of a solvent or diluent, for example in the melt. In most cases, however, the addition of an inert solvent or diluent or of a mixture thereof is advantageous. Examples of such solvents or diluents are, for example, those of the type mentioned under Variant a).

The reaction is advantageously carried out in a temperature range from approximately 0° C. to approximately +100° C., preferably from approximately 20° C. to approximately +80° C.

Variant f):

The reactants can be reacted with one another as such, i.e. without the addition of a solvent or diluent, for example in the melt. In most cases, however, the addition of an inert solvent or diluent or of a mixture thereof is advantageous. Examples of such solvents or diluents are, for example, those of the type mentioned under Variant a).

The reaction is advantageously carried out in a temperature range from approximately 0° C. to approximately +100° C., preferably from approximately 20° C. to approximately +80° C.

Variant g):

The reactants can be reacted with one another as such, i.e. without the addition of a solvent or diluent, for example in the melt. In most cases, however, the addition of an inert solvent or diluent or of a mixture thereof is advantageous. Examples of such solvents or diluents are, for example, those of the type mentioned under Variant a).

The reaction is advantageously carried out in a temperature range from approximately 0° C. to approximately +100° C., preferably from approximately 20° C. to approximately +80° C.

Variant h):

Suitable acid catalysts for facilitating the reaction are, for example, acids of the type mentioned under Variant a).

The reactants can be reacted with one another as such, i.e. without the addition of a solvent or diluent, for example in the melt. In most cases, however, the addition of an inert solvent or diluent or of a mixture thereof is advantageous. Examples of such solvents or diluents are, for example, those of the type mentioned under Variant a).

The reaction is advantageously carried out in a temperature range from approximately 0° C. to approximately +100° C., preferably from approximately 20° C. to approximately +80° C.

Variant i):

Suitable acid catalysts for facilitating the reaction are, for example, acids of the type mentioned under Variant a).

The reactants can be reacted with one another as such, i.e. without the addition of a solvent or diluent, for example in the melt. In most cases, however, the addition of an inert solvent or diluent or of a mixture thereof is advantageous. Examples of such solvents or diluents are, for example, those of the type mentioned under Variant a).

The reaction is advantageously carried out in a temperature range from approximately 0° C. to approximately +100° C., preferably from approximately 20° C. to approximately +80° C.

Variant j):

Suitable reduction catalysts are the transitions metals customarily used, preferably Ni, Pt, Pd, Fe, but also customary hydrogenating agents, such as lithium aluminium hydride, sodium borohydride or diborane.

The reactants can be reacted with one another as such, i.e. without the addition of a solvent or diluent, for example in the melt. In most cases, however, the addition of an inert solvent or diluent or of a mixture thereof is advantageous. Examples of such solvents or diluents are, for example, those of the type mentioned under Variant a).

The reaction is advantageously carried out in a temperature range from approximately 0° C. to approximately +100° C., preferably from approximately 20° C. to approximately +80° C.

Variant k):

The reactants can be reacted with one another as such, i.e. without the addition of a solvent or diluent, for example in the melt. In most cases, however, the addition of an inert solvent or diluent or of a mixture thereof is advantageous. Examples of such solvents or diluents are, for example, those of the type mentioned under Variant a).

The reaction is advantageously carried out in a temperature range from approximately 0° C. to approximately +100° C., preferably from approximately 20° C. to approximately +80° C.

Variant l):

Suitable bases for facilitating the reaction are, for example, those of the type mentioned under Variant c).

The reactants can be reacted with one another as such, i.e. without the addition of a solvent or diluent, for example in the melt. In most cases, however, the addition of an inert solvent or diluent or of a mixture thereof is advantageous. Examples of such solvents or diluents are, for example, those of the type mentioned under Variant c).

The reaction is advantageously carried out in a temperature range from approximately 0° C. to approximately +100° C., preferably from approximately 20° C. to approximately +80° C.

Variant m):

The reactants can be reacted with one another as such, i.e. without the addition of a solvent or diluent, for example in the melt. In most cases, however, the addition of an inert solvent or diluent or of a mixture thereof is advantageous. Examples of such solvents or diluents are, for example, those of the type mentioned under Variant c).

The reaction is advantageously carried out in a temperature range from approximately 0° C. to approximately +100° C., preferably from approximately 20° C. to approximately +80° C.

Variant n):

Suitable bases for facilitating the reaction are, for example, those of the type mentioned under Variant c).

Suitable acid catalysts for facilitating the reaction are, for example, acids of the type mentioned under Variant a).

The reactants can be reacted with one another as such, i.e. without the addition of a solvent or diluent, for example in the melt. In most cases, however, the addition of an inert solvent or diluent or of a mixture thereof is advantageous. Examples of such solvents or diluents are, for example, those of the type mentioned under Variant a).

The reaction is advantageously carried out in a temperature range from approximately 0° C. to approximately +100° C., preferably from approximately 20° C. to approximately +80° C.

Variant o):

Suitable bases for facilitating the reaction are, for example, those of the type mentioned under Variant c).

The reactants can be reacted with one another as such, i.e. without the addition of a solvent or diluent, for example in the melt. In most cases, however, the addition of an inert solvent or diluent or of a mixture thereof is advantageous. Examples of such solvents or diluents are, for example, those of the type mentioned under Variant c).

The reaction is advantageously carried out in a temperature range from approximately 0° C. to approximately +100° C., preferably from approximately 20° C. to approximately +80° C.

Variant p):

Suitable acid catalysts for facilitating the reaction are, for example, acids of the type mentioned under Variant a).

The reactants can be reacted with one another as such, i.e. without the addition of a solvent or diluent, for example in the melt. In most cases, however, the addition of an inert solvent or diluent or of a mixture thereof is advantageous. Examples of such solvents or diluents that may be mentioned are: aromatic, aliphatic and alicyclic hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylene, mesitylene, tetralin, chlorobenzene, dichlorobenzene, bromobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, trichloromethane, tetrachloromethane, dichloroethane, trichloroethene or tetrachloroethene; esters, such as ethyl acetate; ethers, such as diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, tert-butyl methyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, dimethoxydiethyl ether, tetrahydrofuran or dioxane; ketones, such as acetone, methyl ethyl ketone or methyl isobutyl ketone; alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, ethylene glycol or glycerol; amides, such as N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone or hexamethylphosphoric acid triamide; nitriles, such as acetonitrile or propionitrile; and sulfoxides, such as dimethyl sulfoxide. If the reaction is carried out in the presence of an acid catalyst, acids used in excess, for example strong organic carboxylic acids, such as unsubstituted or substituted, for example halo-substituted, C₁ -C₄ alkanecarboxylic acids, for example formic, acetic or propionic acid, may also serve as solvents or diluents.

The reaction is advantageously carried out in a temperature range from approximately 0° C. to approximately +100° C., preferably from approximately 20° C. to approximately +80° C.

Salts of compounds I can be prepared in a manner known per se. For example, acid addition salts of compounds I are obtained by treatment with a suitable acid or a suitable ion exchange reagent, and salts with bases are obtained by treatment with a suitable base or a suitable ion exchange reagent.

Salts of compounds I can be converted into the free compounds I in customary manner: acid addition salts, for example, by treatment with a suitable basic agent or a suitable ion exchange reagent, and salts with bases, for example, by treatment with a suitable acid or a suitable ion exchange reagent.

Salts of compounds I can be converted into different salts of compounds I in a manner known per se: acid addition salts, for example, can be converted into different acid addition salts, for example by treatment of a salt of an inorganic acid, such as a hydrochloride, with a suitable metal salt, such as a sodium, barium or silver salt, of an acid, for example with silver acetate, in a suitable solvent in which an inorganic salt being formed, for example silver chloride, is insoluble and therefore separates from the reaction mixture.

Depending upon the procedure and the reaction conditions, compounds I having saltforming properties can be obtained in free form or in the form of salts.

The compounds I, IV, V, VII, VIII, IX, XV and XVI may be in the form of one of the possible isomers or as a mixture thereof, for example according to the number of asymmetric carbon atoms and the absolute and relative configuration thereof, they may be in the form of pure isomers, such as antipodes and/or diastereoisomers, or in the form of mixtures of isomers, such as mixtures of enantiomers, for example racemates, mixtures of diastereoisomers or mixtures of racemates; the invention relates both to the pure isomers and to all possible mixtures of isomers and this is to be understood hereinbefore and hereinafter, even if stereochemical details are not specifically mentioned in each case.

Mixtures of diastereoisomers and mixtures of racemates of compounds I, IV, V, VII, VIII, IX, XV and XVI that are obtainable in accordance with the process depending upon the starting materials and procedures chosen, or by other means, can be separated into the pure diastereoisomers or racemates in known manner on the basis of the physicochemical differences between the constituents, for example by fractional crystallization, distillation and/or chromatography.

Correspondingly obtainable mixtures of enantiomers, such as racemates, can be separated into the optical antipodes by known methods, for example by recrystallization from an optically active solvent, by chromatography on chiral adsorbents, for example high-pressure liquid chromatography (HPLC) on acetyl cellulose, with the aid of suitable microorganisms, by cleavage with specific immobilized enzymes, via the formation of inclusion compounds, for example using chiral crown ethers, in which case only one enantiomer is complexed.

Apart from by the separation of corresponding mixtures of isomers, it is possible according to the invention to obtain pure diastereoisomers or enantiomers also by generally known methods of diastereoselective or enantioselective synthesis, for example by carrying out the process according to the invention with starting materials having correspondingly suitable stereochemistry.

Advantageously, the biologically more active isomer, for example enantiomer or diastereoisomer, or mixture of isomers, for example mixture of enantiomers, will be isolated or synthesized, insofar as the individual components have different biological activity.

The compounds I, IV, V, VII, VIII, IX, XV and XVI can also be obtained in the form of their hydrates and/or may include other solvents, for example solvents used, where appropriate, for the crystallization of compounds in solid form.

The invention relates to all those forms of the process according to which a compound obtainable as starting material or intermediate at any stage of the process is used as starting material and all or some of the remaining steps are carried out, or a starting material is used in the form of a derivative or a salt and/or its racemates or antipodes or, especially, is formed under the reaction conditions.

In the process of the present invention there are preferably used those starting materials and intermediates which result in the compounds I described at the beginning as being especially valuable.

The invention relates especially to the preparation processes described in Examples P1 to P39.

The invention relates also to those starting materials and intermediates used according to the invention for the preparation of the compounds I or the salts thereof, in each case in free form or in salt form, that are novel, to the use thereof and to processes for the preparation thereof.

In the area of pest control, the compounds I according to the invention are valuable preventive and/or curative active ingredients having a very advantageous biocidal spectrum even at low rates of concentration, while being well tolerated by warm-blooded animals, fish and plants. The compounds of the invention are effective against all or individual development stages of normally sensitive animal pests, but also of resistant animal pests, such as insects and representatives of the order Acarina. The insecticidal or acaricidal action of the compounds of the invention may manifest itself directly, i.e. in the mortality of the pests, which occurs immediately or only after some time, for example during moulting, or indirectly, for example in reduced oviposition and/or hatching rate, good activity corresponding to a mortality of at least 50 to 60%.

The mentioned animal pests include, for example:

of the order Lepidoptera, for example,

Acleris spp., Adoxophyes spp., Aegeria spp., Agrotis spp., Alabama argillaceae, Amylois spp., Anticarsia gemmatalis, Archips spp., Argyrotaenia spp., Autographa spp., Busseola fusca, Cadra cautella, Carposina nipponensis, Chilo spp., Choristoneura spp., Clysia ambiguella, Cnaphalocrocis spp., Cnephasia spp., Cochylis spp., Coleophora spp., Crocidolomia binotalis, Cryptophlebia leucotreta, Cydia spp., Diatraea spp., Diparopsis castanea, Earias spp., Ephestia spp., Eucosma spp., Eupoecilia ambiguella, Euproctis spp., Euxoa spp., Grapholita spp., Hedya nubiferana, Heliothis spp., Hellula undalis, Hyphantria cunea, Keiferia lycopersicella, Leucoptera scitella, Lithocollethis spp., Lobesia botrana, Lymantria spp., Lyonetia spp., Malacosoma spp., Mamestra brassicae, Manduca sexta, Operophtera spp., Ostrinia nubilalis, Pammene spp., Pandemis spp., Panolis flammea, Pectinophora gossypiella, Phthorimaea operculella, Pieris rapae, Pieris spp., Plutella xylostella, Prays spp., Scirpophaga spp., Sesamia spp., Sparganothis spp., Spodoptera spp., Synanthedon spp., Thaumetopoea spp., Tortrix spp., Trichoplusia ni and Yponomeuta spp.;

of the order Coleoptera, for example,

Agriotes spp., Anthonomus spp., Atomaria linearis, Chaetocnema tibialis, Cosmopolites spp., Curculio spp., Dermestes spp., Diabrotica spp., Epilachna spp., Eremnus spp., Leptinotarsa decemlineata, Lissorhoptrus spp., Melolontha spp., Orycaephilus spp., Otiorhynchus spp., Phlyctinus spp., Popillia spp., Psylliodes spp., Rhizopertha spp., Scarabeidae, Sitophilus spp., Sitotroga spp., Tenebrio spp., Tribolium spp. and Trogorma spp.;

of the order Orthoptera, for example,

Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Periplaneta spp. and Schistocerca spp.; of the order Isoptera, for example, Reticulitermes spp.;

of the order Psocoptera, for example,

Liposcelis spp.;

of the order Anoplura, for example,

Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp. and Phylloxera spp.;

of the order Mallophaga, for example,

Damalinea spp. and Trichodectes spp.;

of the order Thysanoptera, for example,

Frankliniella spp., Hercinothrips spp., Taeniothrips spp., Thrips palmi, Thrips tabaci and Scirtothrips aurantii;

of the order Heteroptera, for example,

Cimex spp., Distantiella theobroma, Dysdercus spp., Euchistus spp., Eurygaster spp., Leptocorisa spp., Nezara spp., Piesma spp., Rhodnius spp., Sahlbergella singularis, Scotinophara spp. and Triatoma spp.;

of the order Homoptera, for example,

Aleurothrixus floccosus, Aleyrodes brassicae, Aonidiella spp., Aphididae, Aphis spp., Aspidiotus spp., Bemisia tabaci, Ceroplaster spp., Chrysomphalus aonidium, Chrysomphalus dictyospermi, Coccus hesperidum, Empoasca spp., Eriosoma larigerum, Erythroneura spp., Gascardia spp., Laodelphax spp., Lecanium corni, Lepidosaphes spp., Macrosiphus spp., Myzus spp., Nephotettix spp., Nilaparvata spp., Paratoria spp., Pemphigus spp., Planococcus spp., Pseudaulacaspis spp., Pseudococcus spp., Psylla spp., Pulvinaria aethiopica, Quadraspidiotus spp., Rhopalosiphum spp., Saissetia spp., Scaphoideus spp., Schizaphis spp., Sitobion spp., Trialeurodes vaporariorum, Trioza erytreae and Unaspis citri;

of the order Hymenoptera, for example,

Acromyrmex, Atta spp., Cephus spp., Diprion spp., Diprionidae, Gilpinia polytoma, Hoplocampa spp., Lasius spp., Monomorium pharaonis, Neodiprion spp., Solenopsis spp. and Vespa spp.;

of the order Diptera, for example,

Aedes spp., Antherigona soccata, Bibio hortulanus, Calliphora erythrocephala, Ceratitis spp., Chrysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Drosophila melanogaster, Fannia spp., Gastrophilus spp., Glossina spp., Hypoderma spp., Hyppobosca spp., Liriomyza spp., Lucilia spp., Melanagromyza spp., Musca spp., Oestrus spp., Orseolia spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Rhagoletis pomonella, Sciara spp., Stomoxys spp., Tabanus spp., Tannia spp. and Tipula spp.;

of the order Siphonaptera, for example,

Ceratophyllus spp. and Xenopsylla cheopis;

of the order Thysanura, for example,

Lepisma saccharina; and

of the order Acarina, for example,

Acarus siro, Aceria sheldoni, Aculus schlechtendali, Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Calipitrimerus spp., Chorioptes spp., Dermanyssus gallinae, Eotetranychus carpini, Eriophyes spp., Hyalomma spp., Ixodes spp., Olygonychus pratensis, Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Tarsonemus spp. and Tetranychus spp..

With the compounds according to the invention it is possible to control, i.e. to inhibit or destroy, pests of the mentioned type occurring especially on plants, especially on useful plants and ornamentals in agriculture, in horticulture and in forestry, or on parts of such plants, such as the fruit, blossom, leaves, stems, tubers or roots, while some of the parts of the plants which grow later are also protected against those pests.

Target crops are especially cereals, such as wheat, barley, rye, oats, rice, maize and sorghum; beet, such as sugar beet and fodder beet; fruit, such as pomes, stone fruit and soft fruit, such as apples, pears, plums, peaches, almonds, cherries, or berries, for example strawberries, raspberries or blackberries; leguminous plants, such as beans, lentils, peas and soybeans; oil plants, such as rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans and groundnuts; cucumber plants, such as marrows, cucumber and melons; fibre plants, such as cotton, flax, hemp and jute; citrus fruit, such as oranges, lemons, grapefruit and mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes and paprika; lauraceae, such as avocados, cinnamon and camphor; and tobacco, nuts, coffee, aubergines, sugar cane, tea, pepper, vines, hops, bananas and natural rubber plants, as well as ornamentals.

Further areas of use of the compounds according to the invention are the protection of stored goods and stocks and materials, and also in the hygiene sector, especially the protection of domestic animals and productive livestock against pests of the mentioned type.

The invention therefore relates also to pesticides, such as emulsifiable concentrates, suspension concentrates, directly sprayable or dilutable solutions, coatable pastes, dilute emulsions, wettable powders, soluble powders, dispersible powders, wettable powders, dusts, granules or encapsulations in polymer substances, comprising--at least--one of the compounds of the invention, the type of formulation being chosen in accordance with the intended objectives and prevailing circumstances.

The active ingredient is used in those compositions in pure form, a solid active ingredient, for example, in a specific particle size, or preferably together with--at least--one of the adjuvants customary in formulation technology, such as extenders, for example solvents or solid carriers, or surface-active compounds (surfactants).

Suitable solvents are, for example: optionally partially hydrogenated aromatic hydrocarbons, preferably the fractions of alkylbenzenes containing 8 to 12 carbon atoms, such as xylene mixtures, alkylated naphthalenes or tetrahydronaphthalene, aliphatic or cycloaliphatic hydrocarbons, such as paraffins or cyclohexane, alcohols, such as ethanol, propanol or butanol, glycols and their ethers and esters, such as propylene glycol, dipropylene glycol ether, ethylene glycol or ethylene glycol monomethyl or monoethyl ether, ketones, such as cyclohexanone, isophorone or diacetone alcohol, strongly polar solvents, such as N-methylpyrrolid-2-one, dimethyl sulfoxide or N,N-dimethylformamide, water, vegetable oils or epoxidised vegetable oils, such as rape oil, castor oil, coconut oil or soybean oil or epoxidised rape oil, castor oil, coconut oil or soybean oil, and silicone oils.

The solid carriers used, e.g. for dusts and dispersible powders, are normally natural mineral fillers such as calcite, talcum, kaolin, montmorillonite or attapulgite. In order to improve the physical properties it is also possible to add highly dispersed silicic acids or highly dispersed absorbent polymers. Suitable granulated adsorptive carriers are porous types, such as pumice, broken brick, sepiolite or bentonite; and suitable nonsorbent carriers are calcite or sand. In addition, a great number of granulated materials of inorganic or organic nature can be used, especially dolomite or pulverised plant residues.

Depending on the nature of the compound to be formulated, suitable surface-active compounds are non-ionic, cationic and/or anionic surfactants or mixtures of surfactants having good emulsifying, dispersing and wetting properties. The surfactants listed below are to be regarded merely as examples; many more surfactants customarily employed in formulation technology and suitable for use according to the invention are described in the relevant literature.

Non-ionic surfactants are preferably polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, said derivatives containing 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon moiety and 6 to 18 carbon atoms in the alkyl moiety of the alkylphenols. Further suitable non-ionic surfactants are water-soluble adducts of polyethylene oxide with polypropylene glycol, ethylenediaminopolypropylene glycol and alkylpolypropyle ne glycol containing 1 to 10 carbon atoms in the alkyl chain, which adducts contain 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups. These compounds usually contain 1 to 5 ethylene glycol units per propylene glycol unit . Representative examples of non-ionic surfactants are nonylphenol polyethoxyethanols, castor oil polyglycol ethers, polypropylene/polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol. Fatty acid esters of polyoxyethylene sorbitan, e.g. polyoxyethylene sorbitan trioleate, are also suitable non-ionic surfactants.

Cationic surfactants are preferably quaternary ammonium salts which contain, as substituent, at least one C₈ -C₂₂ alkyl radical and, as further substituents, unsubstituted or halogenated lower alkyl, benzyl or hydroxy-lower alkyl radicals. The salts are preferably in the form of halides, methyl sulfates or ethyl sulfates. Examples are stearyltrimethylammonium chloride and benzyldi(2-chloroethyl)ethylammonium bromide.

Both water-soluble soaps and water-soluble synthetic surface-active compounds are suitable anionic surfactants. Suitable soaps are the alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts of higher fatty acids (C₁₀ -C₂₂), e.g. the sodium or potassium salts of oleic or stearic acid or of natural fatty acid mixtures which can be obtained e.g. from coconut oil or tall oil; mention may also be made of fatty acid methyltaurin salts. More frequently, however, synthetic surfactants are used, especially fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates. The fatty sulfonates or sulfates are usually in the form of alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts and generally contain a C₈ -C₂₂ alkyl radical, which also includes the alkyl moiety of acyl radicals; there may be mentioned by way of example the sodium or calcium salt of lignosulfonic acid, of dodecyl sulfate or of a mixture of fatty alcohol sulfates obtained from natural fatty acids. These compounds also comprise the salts of sulfated and sulfonated fatty alcohol/ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain 2 sulfonic acid groups and one fatty acid radical containing approximately 8 to 22 carbon atoms. Examples of alkylarylsulfonates are the sodium, calcium or triethanolammonium salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid or of a condensate of naphthalenesulfonic acid and formaldehyde. Also suitable are corresponding phosphates, e.g. salts of the phosphoric acid ester of an adduct of p-nonylphenol with 4 to 14 mol of ethylene oxide, or phospholipids.

The compositions usually comprise 0.1 to 99%, preferably 0.1 to 95%, of active ingredient, and 1 to 99.9%, preferably 5 to 99.9%, of--at least--one solid or liquid adjuvant, it generally being possible for 0 to 25%, preferably 0.1 to 20%, of the composition to be surfactants (in each case percentages are by weight). Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ dilute formulations which have considerably lower active ingredient concentrations. Preferred formulations have especially the following composition (throughout, percentages are by weight):

Emulsifiable concentrates:

active ingredient: 1 to 90%, preferably 5 to 20%

surfactant: 1 to 30%, preferably 10 to 20%

solvent: 5 to 98%, preferably 70 to 85%

Dusts:

active ingredient: 0.1 to 10%, preferably 0.1 to 1%

solid carrier: 99.9 to 90%, preferably 99.9 to 99%

Suspension concentrates:

active ingredient: 5 to 75%, preferably 10 to 50%

water: 94 to 24%, preferably 88 to 30%

surfactant: 1 to 40%, preferably 2 to 30%

Wettable powders:

active ingredient: 0.5 to 90%, preferably 1 to 80%

surfactant: 0.5 to 20%, preferably 1 to 15%

solid carrier: 5 to 99%, preferably 15 to 98%

Granules:

active ingredient: 0.5 to 30%, preferably 3 to 15%

solid carrier: 99.5 to 70%, preferably 97 to 85%

The activity of the compositions according to the invention can be substantially broadened and adapted to prevailing circumstances by the addition of other insecticidal or acaricidal active ingredients. Examples of suitable additional insecticidal and acaricidal active ingredients include representatives of the following classes of compounds: organophosphorus compounds, nitrophenols and derivatives, formamidines, acylureas, carbamates, pyrethroids, nitroenamines and derivatives, pyrroles, thioureas and derivatives, chlorinated hydrocarbons, and Bacillus thuringiensis preparations. The compositions according to the invention may also comprise further solid or liquid adjuvants, such as stabilisers, for example vegetable oils or epoxidised vegetable oils (e.g. epoxidised coconut oil, rape oil or soybean oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, as well as fertilisers or other active ingredients for obtaining special effects, for example bactericides, fungicides, nematicides, molluscicides or selective herbicides.

The compositions according to the invention are prepared in known manner, in the absence of adjuvants, for example by grinding, sieving and/or compressing a solid active ingredient or mixture of active ingredients, for example to a specific particle size, and in the presence of at least one adjuvant, for example by intimately mixing and/or grinding the active ingredient or mixture of active ingredients with the adjuvant(s). The invention relates also to that process for the preparation of the compositions according to the invention and to the use of the compounds I for the preparation of those compositions.

The invention relates also to the methods of application of the compositions, i.e. the methods of controlling pests of the mentioned type, such as spraying, atomising, dusting, coating, dressing, scattering or pouring, which are selected in accordance with the intended objectives and prevailing circumstances, and to the use of the compositions for controlling pests of the mentioned type. Typical rates of concentration are from 0.1 to 1000 ppm, preferably from 0.1 to 500 ppm, of active ingredient The rates of application per hectare are generally from 1 to 2000 g of active ingredient per hectare, especially from 10 to 1000 g/ha, preferably from 20 to 600 g/ha.

A preferred method of application in the area of plant protection is application to the foliage of the plants (foliar application), the number of applications and the rate of application depending on the risk of infestation by the pest in question. However, the active ingredient can also penetrate the plants through the roots (systemic action) if the locus of the plants is impregnated with a liquid formulation or if the active ingredient is incorporated in solid form into the locus of the plants, for example into the soil, e.g. in granular form (soil application). In paddy rice crops, such granules may be applied in metered amounts to the flooded rice field.

The compositions according to the invention are also suitable for protecting plant propagation material, e.g. seed, such as fruit, tubers or grains, or plant cuttings, from animal pests. The propagation material can be treated with the formulation before planting: seed, for example, can be dressed before being sown. The compounds of the invention can also be applied to grains (coating), either by impregnating the grains with a liquid formulation or by coating them with a solid formulation. The formulation can also be applied to the planting site when the propagation material is being planted, for example to the seed furrow during sowing. The invention relates also to those methods of treating plant propagation material and to the plant propagation material thus treated.

The following Examples serve to illustrate the invention. They do not limit the invention. Temperatures are given in degrees Celsius. In the Tables "Comp." stands for "Compound Number", "Me" for methyl, "Et" for ethyl, "nPr" for n-propyl, "iPr" for iso-propyl, "cPr" for cyclo-propyl, "tBu" for tert-butyl, "cHex" for cyclo-hexyl and "C₂ H₄ " for CH₂ CH₂.

PREPARATION EXAMPLES Example P1 4-Methyl-1-(pyridin-3-ylmethyleneamino)-imidazolidin-2-one (Compound 1.072 in Table 1)

At 50°, 2.1 g of hydrochloric acid are introduced into a solution of 3.1 g of (4-methyl-2-oxo-imidazolidin-1-yl)acetamide in 40 ml of methanol. After one hour, 2.4 g of pyridine-3-carbaldehyde are added thereto. After 20 minutes, the reaction mixture is concentrated by evaporation and the residue is treated with tetrahydrofuran in a mixer. The crystals are filtered with suction and dried. 4.6 g of 4-methyl-1-(pyridin-3-ylmethyleneamino)imidazolidin-2-one hydrochloride having a melting point of >240° are obtained. 2.3 ml of triethylamine are added to a suspension of 3.6 g of 4-methyl-1-(pyridin-3-ylmethyleneamino)-imidazolidin-2-one hydrochloride in 100 ml of tetrahydrofuran and the reaction mixture is heated under reflux for 5 minutes and then stirred for one hour. The triethylamine hydrochloride that has formed is filtered off with suction and 300 ml of hexane are added to the filtrate. The crystals that have precipitated are filtered with suction and dried. They are crystals of the title compound having a melting point of 189°-195°.

EXAMPLE P2 4-(Pyridin-3-ylmethyleneamino)-1,2,4-triazol-3-one (Compound 1.117 in Table 1)

A mixture of 4 g of 4-amino-1,2,4-triazol-3-one and 100 ml of alcohol is heated to the reflux temperature and 4.3 g of pyridine-3-carbaldehyde and 2 drops of 6N hydrochloric acid are added thereto. After 30 minutes under reflux the reaction mixture is cooled to 20°. The product that has precipitated is then filtered off with suction and dried under a high vacuum. 4.6 g of the title compound having a melting point of 264°-265° are obtained.

EXAMPLE P3 4-(Pyridin-3-ylmethyleneamino)-5-methyl-1,2,4-triazol-3-one (Compound 1.273 in Table 1)

A mixture of 5.7 g of 4-amino-5-methyl-1,2,4-triazol-3-one and 100 ml of alcohol is heated to the reflux temperature and 5.4 g of pyridine-3-carbaldehyde and 2 drops of 6N hydrochloric acid are added thereto. After 14 hours under reflux the reaction mixture is cooled to 20°. The product that has precipitated is then filtered off with suction and dried under a high vacuum. 3.4 g of the title compound having a melting point of 208°-210° are obtained.

EXAMPLE P4 2-Acetyl-4-(pyridin-3-ylmethyleneamino)-1,2,4-triazol-3-one (Compound 1.115 in Table 1)

2.4 g of acetyl chloride are added to a suspension of 3.8 g of 4-(pyridin-3-ylmethyleneamino)-1,2,4-triazol-3-one in 50 ml of pyridine. The resulting solution is stirred for 14 hours at 20° and then concentrated by evaporation. Water is added to the residue and extraction is carried out with chloroform. The organic phase is concentrated by evaporation and the residue is stirred with ether. The crystals are filtered off with suction and then dried under a high vacuum. 4 g of the title compound having a melting point of 164°-166° are thus obtained.

EXAMPLE P5 4-(Pyridin-3-ylmethyleneamino)-1,2,4-triazol-3-one-2-carboxylic acid dimethylamide (Compound 1.116 in Table 1)

3.2 g of dimethylcarbamoyl chloride are added to a suspension of 3.8 g of 4-(pyridin-3-ylmethyleneamino)-1,2,4-triazol-3-one in 50 ml of pyridine. The resulting solution is stirred for 14 hours at 20° and then concentrated by evaporation. Water is added to the residue. The crystals that have precipitated are filtered off with suction and dried under a high vacuum. 3.6 g of crystals of the title compound having a melting point of 181°-182° are obtained.

EXAMPLE P6 5-Methyl-2-oxo-2,3-dihydro-1-(pyridin-3-ylmethyleneamino)-imidazole (Compound 1.121 in Table 1) and 4-methyl-2-oxo-2,3-dihydro-1-(pyridin-3-ylmethyleneamino)-imidazole (Compound 1.138 in Table 1)

A suspension of 18.4 g of 4-methyl-3- (pyridin-3-ylmethylene)amino!-1- (pyridin-3-ylmethylene)amino!-1,3-dihydroimidazol-2-one in 400 ml of tetrahydrofuran is heated to 60° and then 8.3 g of potassium tertiary butoxide are added thereto. When the foaming has subsided, the reaction mixture is cooled to 20° and poured onto 500 ml of saturated aqueous sodium chloride solution. The phases are separated and the aqueous phase is extracted with four times 150 ml of tetrahydrofuran. The organic phase is collected and washed twice with 150 ml of saturated aqueous sodium chloride solution each time, dried with magnesium sulfate and concentrated by evaporation. The residue is stirred with a small amount of methylene chloride. The crystals are filtered off with suction and dried. 3.4 g of crystals having a melting point of 168°-177° are obtained. They are crystals of 4-methyl-2-oxo-2,3-dihydro-1-(pyridin-3-ylmethyleneamino)-imidazole. The mother liquor is concentrated by evaporation and chromatographed on silica gel using ethyl acetate. There are obtained on the one hand 3.8 g of yellowish crystals of 4-methyl-2-oxo-2,3-dihydro-1-(pyridin-3-ylmethylenearnino)-imidazole having a melting point of 177°-179°, and on the other hand 0.7 g of 5-methyl-2-oxo-2,3-dihydro-1-(pyridin-3-ylmethyleneamino)-imidazole having a melting point of 200°-202°.

EXAMPLE P7 3,4-Dimethyl-1-(pyridin-3-ylmethyleneamino)-imidazolidin-2-one (Compound 1.074 in Table 1)

2.3 g of pyridine-3-carbaldehyde are added at room temperature to a solution of 3.6 g of 1-amino-3,4-dimethylimidazolidin-2-one hydrochloride in 25 ml of methanol. The solution is concentrated by evaporation and the residue is stirred with tetrahydrofuran. 4.6 g of 3,4-dimethyl-1-(pyridin-3-ylmethyleneamino)-imidazolidin-2-one hydrochloride having a melting point of 232°-236° are obtained. 2.3 g of triethylamine are added to a suspension of 4.4 g of 3,4-dimethyl-1-(pyridin-3-ylmethyleneamino)-imidazolidin-2-one hydrochloride in 100 ml of tetrahydrofuran and after 20 minutes under reflux the reaction mixture is filtered while hot. 300 ml of hexane are added to the filtrate. The crystals that have precipitated are filtered off with suction and dried. 2.5 g of the title compound having a melting point of 126°-129° are obtained.

EXAMPLE P8 6-Methyl4-(pyridin-3-ylmethyleneamino)-1,4,5,6-tetrahydro-1,2,4-triazin-3(2H)-one (Compound 1.291 in Table 1)

2.2 g of pyridine-3-carbaldehyde and 2 drops of sulfuric acid are added to a solution of 3 g of 4-amino-6-methyl-3-oxo-1,4,5,6-tetrahydro-1,2,4-triazine in 30 ml of ethanol. The reaction mixture is then maintained under reflux for 90 minutes and then the resulting suspension is cooled to 200°, filtered and dried. 4.1 g of the title compound having a melting point of 235°-237° are obtained.

EXAMPLE P9 6-Ethoxymethyl-4-(pyridin-3-ylmethyleneamino)-4,5-dihydro-2H- 1,2,4!-triazin-3-one (Compound 1.335 in Table 1)

2 g of (6-ethoxymethyl-3-oxo-2,5-dihydro-3H- 1,3,4!triazin-4-yl)-thiocarbamic acid O-methyl ester (Comp. 9.073) are placed in a round-bottomed flask, 6 ml of sulfuric acid are added thereto and the reaction mixture is then heated to 60°. After one hour the reaction mixture is poured onto 50 g of ice and adjusted to pH 10 with concentrated sodium hydroxide solution and then to pH 4 with hydrochloric acid. 1.1 g of 3-pyridine aldehyde is then added thereto. After 30 minutes the reaction mixture is extracted three times with 50 ml of methylene chloride and concentrated by evaporation. The residue is stirred with ether/isopropanol. 0.8 g of the title compound in the form of yellowish crystals having a melting point of 156°-158° is thus obtained.

EXAMPLE P10

The other compounds listed in Tables 1, 1a and 1b can also be prepared in a manner analogous to that described in Examples P1 to P9.

                                      TABLE 1                                      __________________________________________________________________________      ##STR18##                                                                     Comp.                                                                              A        m B        D        E       G                                     __________________________________________________________________________     1.001                                                                              CS       0          NH       NH      CS                                    1.002                                                                              CS       0          NH       NH      CO                                    1.003                                                                              CO       1 CMe      N        NH      CS                                    1.004                                                                              CO       1 C(C.sub.2 H.sub.4 iPr)                                                                  N        NH      CS                                    1.005                                                                              CO       1 C(CH.sub.2 iPr)                                                                         N        NH      CS                                    1.006                                                                              CO       1 CtBu     N        NH      CS                                    1.007                                                                              CO       1 CtBu     N        NH      CO                                    1.008                                                                              CO       1 CcPr     N        NH      CS                                    1.009                                                                              CO       1 CcHex    N        NH      CS                                    1.010                                                                              CO       1 NCH.sub.2 -cHex                                                                         CO       NH      CO                                    1.011                                                                              CO       1 CH.sub.2 CO       NH      CO                                    1.012                                                                              CO       1 CH.sub.2 CH.sub.2 NH      CO                                    1.013                                                                              CO       1 CH.sub.2 CMe.sub.2                                                                               NH      CO                                    1.014                                                                              CO       1 CH       CMe      NH      CO                                    1.015                                                                              CO       1 CH       N        NH      CS                                    1.016                                                                              CO       1 CH       CCF.sub.3                                                                               NH      CNH                                   1.017                                                                              CO       1 CMe.sub.2                                                                               CO       NH      CO                                    1.018                                                                              CO       1 CMe.sub.2                                                                               CH.sub.2 NH      CO                                    1.019                                                                              CO       1 CMe      N        NH      CO                                    1.020                                                                              CO       1 CtBu     N        NC.sub.2 H.sub.4 F                                                                     CS                                    1.021                                                                              CO       1 CEt      N        NH      CS                                    1.022                                                                              CO       0          CO       NH      CO                                    1.023                                                                              CO       0          NH       NH      CO                                    1.024                                                                              CO       0          CH.sub.2 S       CS                                    1.025                                                                              CO       0          CHCH.sub.2 COOMe                                                                        NH      CS                                    1.026                                                                              CO       0          CHC.sub.2 H.sub.4 COOMe                                                                 NH      CS                                    1.027                                                                              CO       0          NH       NH      CO                                    1.028                                                                              CO       0          CMeCHCMe.sub.2                                                                          NH      CO                                    1.029                                                                              CO       0          CMeCH.sub.2 CMe.sub.2                                                                   NH      CO                                    1.030                                                                              CO       0          CH.sub.2 NH      CS                                    1.031                                                                              CO       0          CMe.sub.2                                                                               NH      CO                                    1.032                                                                              CH.sub.2 0          CO       NMe     CS                                    1.033                                                                              CH.sub.2 0          CO       NiPr    CS                                    1.034                                                                              CH.sub.2 0          CO       NEt     CS                                    1.035                                                                              CH.sub.2 0          CO       NH      CO                                    1.036                                                                              CH.sub.2 0          CO       NH      CS                                    1.037                                                                              CH.sub.2 1 CMe.sub.2                                                                               CO       NH      CO                                    1.038                                                                              CH.sub.2 0          CO       NH      CO                                    1.039                                                                              CH.sub.2 1 CH.sub.2 CO       NH      CO                                    1.040                                                                              CH.sub.2 0          CH.sub.2 O       CO                                    1.041                                                                              CH.sub.2 0          CH.sub.2 NH      CO                                    1.042                                                                              CH.sub.2 0          CH.sub.2 NH      CS                                    1.043                                                                              CH.sub.2 0          CH.sub.2 CH.sub.2                                                                               CO                                    1.044                                                                              CH.sub.2 0          CH.sub.2 NH      CO                                    1.045                                                                              CH.sub.2 0          CH.sub.2 NH      CO                                    1.046                                                                              CH.sub.2 1 CH.sub.2 CH.sub.2 NH      CO                                    1.047                                                                              CH.sub.2 1 CMe.sub.2                                                                               CH.sub.2 NH      CO                                    1.048                                                                              CH.sub.2 1 CMe.sub.2                                                                               CH.sub.2 NH      CO                                    1.049                                                                              CH.sub.2 1 C(OMe).sub.2                                                                            CH.sub.2 NH      CO                                    1.050                                                                              CH.sub.2 1 C(OEt).sub.2                                                                            CH.sub.2 NH      CO                                    1.051                                                                              CH.sub.2 1 C(CH.sub.2 OH).sub.2                                                                    CH.sub.2 NH      CO                                    1.052                                                                              CH.sub.2 1 CO       CH.sub.2 NH      CO                                    1.053                                                                              CH.sub.2 1 CHOH     CH.sub.2 NH      CO                                    1.054                                                                              CH.sub.2 1 O        CH.sub.2 NH      CO                                    1.055                                                                              CH.sub.2 1 NMe      CH.sub.2 NH      CO                                    1.056                                                                              CH.sub.2 0          CH.sub.2 NH      CO                                    1.057                                                                              CH.sub.2 0          CH.sub.2 NMe     CO                                    1.058                                                                              CH.sub.2 0          CH.sub.2 NCOMe   CO                                    1.059                                                                              CH.sub.2 0          CH.sub.2 NCOEt   CO                                    1.060                                                                              CH.sub.2 0          CH.sub.2 NCO-nPr CO                                    1.061                                                                              CH.sub.2 0          CH.sub.2 NCOCH.sub.2 OMe                                                                        CO                                    1.062                                                                              CH.sub.2 0          CH.sub.2 NCOCHMe.sub.2                                                                          CO                                    1.063                                                                              CH.sub.2 1 CH.sub.2 CH.sub.2 NH      CO                                    1.064                                                                              CH.sub.2 1 CH.sub.2 CH.sub.2 NH      CO                                    1.065                                                                              CH.sub.2 1 CH.sub.2 CH.sub.2 NMe     CO                                    1.066                                                                              CH.sub.2 1 CH.sub.2 CH.sub.2 NCOMe   CO                                    1.067                                                                              CH.sub.2 1 CH.sub.2 CH.sub.2 NCOEt   CO                                    1.068                                                                              CH.sub.2 1 CH.sub.2 CH.sub.2 NCO-nPr CO                                    1.069                                                                              CH.sub.2 1 CH.sub.2 CH.sub.2 NCOCH.sub.2 OMe                                                                        CO                                    1.070                                                                              CH.sub.2 1 CH.sub.2 CH.sub.2 NCOCHMe.sub.2                                                                          CO                                    1.071                                                                              CH.sub.2 1 CH       CH       NH      CO                                    1.072                                                                              CH.sub.2 0          CHMe     NH      CO                                    1.073                                                                              CH.sub.2 0          CHMe     NH      CO                                    1.074                                                                              CH.sub.2 0          CHMe     NMe     CO                                    1.075                                                                              CH.sub.2 0          CHMe     NCOMe   CO                                    1.076                                                                              CH.sub.2 0          CHMe     NCOEt   CO                                    1.077                                                                              CH.sub.2 0          CHMe     NCO-nPr CO                                    1.078                                                                              CH.sub.2 0          CHMe     NCOCH.sub.2 OMe                                                                        CO                                    1.079                                                                              CH.sub.2 0          CHMe     NCOCHMe.sub.2                                                                          CO                                    1.080                                                                              CH.sub.2 1 CH.sub.2 CHMe     NH      CO                                    1.081                                                                              CH.sub.2 1 CH.sub.2 CHMe     NH      CO                                    1.082                                                                              CH.sub.2 1 CH.sub.2 CHMe     NMe     CO                                    1.083                                                                              CH.sub.2 1 CH.sub.2 CHMe     NCOMe   CO                                    1.084                                                                              CH.sub.2 1 CH.sub.2 CHMe     NCOEt   CO                                    1.085                                                                              CH.sub.2 1 CH.sub.2 CHMe     NCO-nPr CO                                    1.086                                                                              CH.sub.2 1 CH.sub.2 CHMe     NCOCH.sub.2 OMe                                                                        CO                                    1.087                                                                              CH.sub.2 1 CH.sub.2 CHMe     NCOCHMe.sub.2                                                                          CO                                    1.088                                                                              CH.sub.2 0          CHCH.sub.2 OMe                                                                          NH      CO                                    1.089                                                                              CH.sub.2 1 CH.sub.2 CHCH.sub.2 OMe                                                                          NH      CO                                    1.090                                                                              CH.sub.2 0          CH-tBu   NH      CO                                    1.091                                                                              CH.sub.2 1 CH.sub.2 CH-tBu   NH      CO                                    1.092                                                                              CH.sub.2 0          CH-iPr   NH      CO                                    1.093                                                                              CH.sub.2 1 CH.sub.2 CH-iPr   NH      CO                                    1.094                                                                              CH.sub.2 0          CH-cPr   NH      CO                                    1.095                                                                              CH.sub.2 1 CH.sub.2 CH-cPr   NH      CO                                    1.096                                                                              CH.sub.2 0          CHEt     NH      CO                                    1.098                                                                              CH.sub.2 0          CHEt     NMe     CO                                    1.099                                                                              CH.sub.2 0          CHEt     NCOMe   CO                                    1.100                                                                              CH.sub.2 0          CHEt     NCOEt   CO                                    1.101                                                                              CH.sub.2 0          CHEt     NCO-nPr CO                                    1.102                                                                              CH.sub.2 0          CHEt     NCOCH.sub.2 OMe                                                                        CO                                    1.103                                                                              CH.sub.2 0          CHEt     NCOCHMe.sub.2                                                                          CO                                    1.104                                                                              CH.sub.2 1 CH.sub.2 CHEt     NH      CO                                    1.106                                                                              CH.sub.2 1 CH.sub.2 CHEt     NMe     CO                                    1.107                                                                              CH.sub.2 1 CH.sub.2 CHEt     NCOMe   CO                                    1.108                                                                              CH.sub.2 1 CH.sub.2 CHEt     NCOEt   CO                                    1.109                                                                              CH.sub.2 1 CH.sub.2 CHEt     NCO-nPr CO                                    1.110                                                                              CH.sub.2 1 CH.sub.2 CHEt     NCOCH.sub.2 OMe                                                                        CO                                    1.111                                                                              CH.sub.2 1 CH.sub.2 CHEt     NCOCHMe.sub.2                                                                          CO                                    1.112                                                                              CH.sub.2 1 CMe      CH       NH      CO                                    1.113                                                                              CH.sub.2 1 CEt      CH       NH      CO                                    1.114                                                                              CH.sub.2 1 CH       C(t-Bu)  NMe     CO                                    1.115                                                                              CH       0          N        NCOCH.sub.3                                                                            CO                                    1.116                                                                              CH       0          N        NCONMe.sub.2                                                                           CNH                                   1.117                                                                              CH       0          N        NH      CO                                    1.118                                                                              CH       1 CH       NH       NH      CO                                    1.119                                                                              CH       1 CMe      CH.sub.2 NH      CO                                    1.120                                                                              CH       1 CEt      CH.sub.2 NH      CO                                    1.121                                                                              CH       0          CMe      NH      CO                                    1.122                                                                              CH       1 CH       CHMe     NH      CO                                    1.123                                                                              CH       0          CtBu     NH      CO                                    1.124                                                                              CHMe     0          CH.sub.2 NH      CO                                    1.125                                                                              CHMe     0          CH.sub.2 NMe     CO                                    1.126                                                                              CHMe     0          CH.sub.2 NCOMe   CO                                    1.127                                                                              CHMe     0          CH.sub.2 NCOEt   CO                                    1.128                                                                              CHMe     0          CH.sub.2 NCOnPr  CO                                    1.129                                                                              CHMe     0          CH.sub.2 NCOCH.sub.2 OMe                                                                        CO                                    1.130                                                                              CHMe     0          CH.sub.2 NCOCHMe.sub.2                                                                          CO                                    1.131                                                                              CHMe     1 CH.sub.2 CH.sub.2 NH      CO                                    1.132                                                                              CHMe     1 CH.sub.2 CH.sub.2 NMe     CO                                    1.133                                                                              CHMe     1 CH.sub.2 CH.sub.2 NCOMe   CO                                    1.134                                                                              CHMe     1 CH.sub.2 CH.sub.2 NCOEt   CO                                    1.135                                                                              CHMe     1 CH.sub.2 CH.sub.2 NCOnPr  CO                                    1.136                                                                              CHMe     1 CH.sub.2 CH.sub.2 NCOCH.sub.2 OMe                                                                        CO                                    1.137                                                                              CHMe     1 CH.sub.2 CH.sub.2 NCOCHMe.sub.2                                                                          CO                                    1.138                                                                              CMe      0          C        NCH.sub.3                                                                              CO                                    1.139                                                                              CHMe     1 CH       CH       NH      CO                                    1.140                                                                              CHMe     0          CHMe     NH      CO                                    1.141                                                                              CHMe     0          CHMe     NMe     CO                                    1.142                                                                              CHMe     0          CHMe     NCOMe   CO                                    1.143                                                                              CHMe     0          CHMe     NCOEt   CO                                    1.144                                                                              CHMe     0          CHMe     NCOnPr  CO                                    1.145                                                                              CHMe     0          CHMe     NCOCH.sub.2 OMe                                                                        CO                                    1.146                                                                              CHMe     0          CHMe     NCOCHMe.sub.2                                                                          CO                                    1.147                                                                              CHMe     1 CH.sub.2 CHMe     NH      CO                                    1.148                                                                              CHMe     1 CH.sub.2 CHMe     NMe     CO                                    1.149                                                                              CHMe     1 CH.sub.2 CHMe     NCOMe   CO                                    1.150                                                                              CHMe     1 CH.sub.2 CHMe     NCOEt   CO                                    1.151                                                                              CHMe     1 CH.sub.2 CHMe     NCOnPr  CO                                    1.152                                                                              CHMe     1 CH.sub.2 CHMe     NCOCH.sub.2 OMe                                                                        CO                                    1.153                                                                              CHMe     1 CH.sub.2 CHMe     NCOCHMe.sub.2                                                                          CO                                    1.154                                                                              CHMe     0          CHEt     NH      CO                                    1.155                                                                              CHMe     0          CHEt     NMe     CO                                    1.156                                                                              CHMe     0          CHEt     NCOMe   CO                                    1.157                                                                              CHMe     0          CHEt     NCOEt   CO                                    1.158                                                                              CHMe     0          CHEt     NCOnPr  CO                                    1.159                                                                              CHMe     0          CHEt     NCOCH.sub.2 OMe                                                                        CO                                    1.160                                                                              CHMe     0          CHEt     NCOCHMe.sub.2                                                                          CO                                    1.161                                                                              CHMe     1 CH.sub.2 CHEt     NH      CO                                    1.162                                                                              CHMe     1 CH.sub.2 CHEt     NMe     CO                                    1.163                                                                              CHMe     1 CH.sub.2 CHEt     NCOMe   CO                                    1.164                                                                              CHMe     1 CH.sub.2 CHEt     NCOEt   CO                                    1.165                                                                              CHMe     1 CH.sub.2 CHEt     NCOnPr  CO                                    1.166                                                                              CHMe     1 CH.sub.2 CHEt     NCOCH.sub.2 OMe                                                                        CO                                    1.167                                                                              CHMe     1 CH.sub.2 CHEt     NCOCHMe.sub.2                                                                          CO                                    1.168                                                                              CHCH.sub.2 OMe                                                                          0          CH.sub.2 NH      CO                                    1.169                                                                              CHCH.sub.2 OMe                                                                          1 CH.sub.2 CH.sub.2 NH      CO                                    1.170                                                                              CHtBu    0          CH.sub.2 NH      CO                                    1.171                                                                              CHtBu    1 CH.sub.2 CH.sub.2 NH      CO                                    1.172                                                                              CHiPr    0          CH.sub.2 NH      CO                                    1.173                                                                              CHiPr    1 CH.sub.2 CH.sub.2 NH      CO                                    1.174                                                                              CHiPr    0          CH.sub.2 NH      CO                                    1.175                                                                              CHiPr    0          CH.sub.2 NMe     CO                                    1.176                                                                              CHiPr    0          CH.sub.2 NCOMe   CO                                    1.177                                                                              CHiPr    0          CH.sub.2 NCOEt   CO                                    1.178                                                                              CHiPr    0          CH.sub.2 NCOnPr  CO                                    1.179                                                                              CHiPr    0          CH.sub.2 NCOCH.sub.2 OMe                                                                        CO                                    1.180                                                                              CHiPr    0          CH.sub.2 NCOCHMe.sub.2                                                                          CO                                    1.181                                                                              CHiPr    1 CH.sub.2 CH.sub.2 NH      CO                                    1.182                                                                              CHiPr    1 CH.sub.2 CH.sub.2 NMe     CO                                    1.183                                                                              CHiPr    1 CH.sub.2 CH.sub.2 NCOMe   CO                                    1.184                                                                              CHiPr    1 CH.sub.2 CH.sub.2 NCOEt   CO                                    1.185                                                                              CHiPr    1 CH.sub.2 CH.sub.2 NCO-nPr CO                                    1.186                                                                              CHiPr    1 CH.sub.2 CH.sub.2 NCOCH.sub.2 OMe                                                                        CO                                    1.187                                                                              CHiPr    1 CH.sub.2 CH.sub.2 NCOCHMe.sub.2                                                                          CO                                    1.188                                                                              CHiPr    0          CHMe     NH      CO                                    1.189                                                                              CHiPr    0          CHMe     NMe     CO                                    1.190                                                                              CHiPr    0          CHMe     NCOMe   CO                                    1.191                                                                              CHiPr    0          CHMe     NCOEt   CO                                    1.192                                                                              CH(iPr   0          CHMe     NCOnPr  CO                                    1.193                                                                              CHiPr    0          CHMe     NCOCH.sub.2 OMe                                                                        CO                                    1.194                                                                              CHiPr    0          CHMe     NCOCHMe.sub.2                                                                          CO                                    1.195                                                                              CHiPr    1 CH.sub.2 CHMe     NH      CO                                    1.196                                                                              CHiPr    1 CH.sub.2 CHMe     NMe     CO                                    1.197                                                                              CHiPr    1 CH.sub.2 CHMe     NCOMe   CO                                    1.198                                                                              CHiPr    1 CH.sub.2 CHMe     NCOEt   CO                                    1.199                                                                              CHiPr    1 CH.sub.2 CHMe     NCOnPr  CO                                    1.200                                                                              CHiPr    1 CH.sub.2 CHMe     NCOCH.sub.2 OMe                                                                        CO                                    1.201                                                                              CHiPr    1 CH.sub.2 CHMe     NCOCHMe.sub.2                                                                          CO                                    1.202                                                                              CHiPr    0          CHEt     NH      CO                                    1.203                                                                              CHiPr    0          CHEt     NMe     CO                                    1.204                                                                              CHiPr    0          CHEt     NCOMe   CO                                    1.205                                                                              CHiPr    0          CHEt     NCOEt   CO                                    1.206                                                                              CHiPr    0          CHEt     NCOnPr  CO                                    1.207                                                                              CHiPr    0          CHEt     NCOCH.sub.2 OMe                                                                        CO                                    1.208                                                                              CHiPr    0          CHEt     NCOCHMe.sub.2                                                                          CO                                    1.209                                                                              CHiPr    1 CH.sub.2 CHEt     NH      CO                                    1.210                                                                              CHiPr    1 CH.sub.2 CHEt     NMe     CO                                    1.211                                                                              CHiPr    1 CH.sub.2 CHEt     NCOMe   CO                                    1.212                                                                              CHiPr    1 CH.sub.2 CHEt     NCOEt   CO                                    1.213                                                                              CHiPr    1 CH.sub.2 CHEt     NCOnPr  CO                                    1.214                                                                              CHiPr    1 CH.sub.2 CHEt     NCOCH.sub.2 OMe                                                                        CO                                    1.215                                                                              CHiPr    1 CH.sub.2 CHEt     NCOCHMe.sub.2                                                                          CO                                    1.216                                                                              CHcPr    0          CH.sub.2 NH      CO                                    1.217                                                                              CHcPr    1 CH.sub.2 CH.sub.2 NH      CO                                    1.218                                                                              CHEt     0          CH.sub.2 NH      CO                                    1.219                                                                              CHEt     1 CH.sub.2 CH.sub.2 NH      CO                                    1.220                                                                              CHEt     0          CH.sub.2 NH      CO                                    1.221                                                                              CHEt     0          CH.sub.2 NMe     CO                                    1.222                                                                              CHEt     0          CH.sub.2 NCOMe   CO                                    1.223                                                                              CHEt     0          CH.sub.2 NCOEt   CO                                    1.224                                                                              CHEt     0          CH.sub.2 NCOnPr  CO                                    1.225                                                                              CHEt     0          CH.sub.2 NCOCH.sub.2 OMe                                                                        CO                                    1.226                                                                              CHEt     0          CH.sub.2 NCOCHMe.sub.2                                                                          CO                                    1.227                                                                              CHEt     1 CH.sub.2 CH.sub.2 NH      CO                                    1.228                                                                              CHEt     1 CH.sub.2 CH.sub.2 NMe     CO                                    1.229                                                                              CHEt     1 CH.sub.2 CH.sub.2 NCOMe   CO                                    1.230                                                                              CHEt     1 CH.sub.2 CH.sub.2 NCOEt   CO                                    1.231                                                                              CHEt     1 CH.sub.2 CH.sub.2 NCOnPr  CO                                    1.232                                                                              CHEt     1 CH.sub.2 CH.sub.2 NCOCH.sub.2 OMe                                                                        CO                                    1.233                                                                              CHEt     1 CH.sub.2 CH.sub.2 NCOCHMe.sub.2                                                                          CO                                    1.234                                                                              CHEt     0          CHMe     NH      CO                                    1.235                                                                              CHEt     0          CHMe     NMe     CO                                    1.236                                                                              CHEt     0          CHMe     NCOMe   CO                                    1.237                                                                              CHEt     0          CHMe     NCOEt   CO                                    1.238                                                                              CHEt     0          CHMe     NCO-nPr CO                                    1.239                                                                              CHEt     0          CHMe     NCOCH.sub.2 OMe                                                                        CO                                    1.240                                                                              CHEt     0          CHMe     NCOCHMe.sub.2                                                                          CO                                    1.241                                                                              CHEt     1 CH.sub.2 CHMe     NH      CO                                    1.242                                                                              CHEt     1 CH.sub.2 CHMe     NMe     CO                                    1.243                                                                              CHEt     1 CH.sub.2 CHMe     NCOMe   CO                                    1.244                                                                              CHEt     1 CH.sub.2 CHMe     NCOEt   CO                                    1.245                                                                              CHEt     1 CH.sub.2 CHMe     NCOnPr  CO                                    1.246                                                                              CHEt     1 CH.sub.2 CHMe     NCOCH.sub.2 OMe                                                                        CO                                    1.247                                                                              CHEt     1 CH.sub.2 CHMe     NCOCHMe.sub.2                                                                          CO                                    1.248                                                                              CHEt     0          CHEt     NH      CO                                    1.249                                                                              CHEt     0          CHEt     NMe     CO                                    1.250                                                                              CHEt     0          CHEt     NCOMe   CO                                    1.251                                                                              CHEt     0          CHEt     NCOEt   CO                                    1.252                                                                              CHEt     0          CHEt     NCOnPr  CO                                    1.253                                                                              CHEt     0          CHEt     NCOCH.sub.2 OMe                                                                        CO                                    1.254                                                                              CHEt     0          CHEt     NCOCHMe.sub.2                                                                          CO                                    1.255                                                                              CHEt     1 CH.sub.2 CHEt     NH      CO                                    1.256                                                                              CHEt     1 CH.sub.2 CHEt     NMe     CO                                    1.257                                                                              CHEt     1 CH.sub.2 CHEt     NCOMe   CO                                    1.258                                                                              CHEt     1 CH.sub.2 CHEt     NCOEt   CO                                    1.259                                                                              CHEt     1 CH.sub.2 CHEt     NCOnPr  CO                                    1.260                                                                              CHEt     1 CH.sub.2 CHEt     NCOCH.sub.2 OMe                                                                        CO                                    1.261                                                                              CHEt     1 CH.sub.2 CHEt     NCOCHMe.sub.2                                                                          CO                                    1.262                                                                              CSMe     1 N        CO       NMe     CO                                    1.263                                                                              CNHCOOEt 0          N        NH      CS                                    1.264                                                                              CNHCOOMe 0          N        NH      CS                                    1.265                                                                              CNHMe    1 N        CO       NMe     CO                                    1.266                                                                              CMe.sub.2                                                                               0          CO       NH      CO                                    1.267                                                                              CMe.sub.2                                                                               1 CH.sub.2 CO       NH      CO                                    1.268                                                                              CMe.sub.2                                                                               0          CH.sub.2 NH      CO                                    1.269                                                                              CMe.sub.2                                                                               1 CH.sub.2 CH.sub.2 NH      CO                                    1.270                                                                              CMe      0          CCOOEt   S       CNH                                   1.271                                                                              CMe      0          N        NH      CS                                    1.273                                                                              CMe      0          N        NH      CO                                    1.274                                                                              CMe      1 CH       NH       NH      CO                                    1.275                                                                              CMe      0          CH       S       CNH                                   1.276                                                                              CHMe     0          CH.sub.2 NH      CO                                    1.277                                                                              CMe      1 CH       CH.sub.2 NH      CO                                    1.278                                                                              CCH.sub.2 OMe                                                                           0          N        NH      CS                                    1.279                                                                              CCH.sub.2 OEt                                                                           0          N        NH      CS                                    1.280                                                                              CCH.sub.2 iPr                                                                           0          N        NH      CS                                    1.281                                                                              CCF.sub.3                                                                               0          N        NH      CS                                    1.282                                                                              CcHex    0          N        NH      CS                                    1.283                                                                              CiPr     0          N        NH      CS                                    1.284                                                                              CcPr     0          N        NH      CS                                    1.285                                                                              CEt      0          N        NH      CS                                    1.286                                                                              CEt      0          N        NH      CO                                    1.287                                                                              CC.sub.2 F.sub.5                                                                        0          N        NH      CS                                    1.288                                                                              CBr      0          N        NH      CS                                    1.289                                                                              C(NH)    0          CMe.sub.2                                                                               NH      CO                                    1.290                                                                              C(NH)    1 CH       CMe      NH      CO                                    1.291                                                                              CH.sub.2 1 CHMe     NH       NH      CO                                    1.292                                                                              CH.sub.2 1 CHEt     NH       NH      CO                                    1.293                                                                              CH.sub.2 1 CHcPr    NH       NH      CO                                    1.294                                                                              CH.sub.2 1 CHtBu    NH       NH      CO                                    1.295                                                                              CH.sub.2 1 CHCH.sub.2 OMe                                                                          NH       NH      CO                                    1.296                                                                              CHMe     1 CHMe     NH       NH      CO                                    1.297                                                                              CHMe     1 CHEt     NH       NH      CO                                    1.298                                                                              CHMe     1 CHcPr    NH       NH      CO                                    1.299                                                                              CHMe     1 CHtBu    NH       NH      CO                                    1.300                                                                              CHMe     1 CHCH.sub.2 OMe                                                                          NH       NH      CO                                    1.301                                                                              CMe.sub.2                                                                               1 CHMe     NH       NH      CO                                    1.302                                                                              CMe.sub.2                                                                               1 CHEt     NH       NH      CO                                    1.303                                                                              CMe.sub.2                                                                               1 CHCPr    NH       NH      CO                                    1.304                                                                              CMe.sub.2                                                                               1 CHtBu    NH       NH      CO                                    1.305                                                                              CMe.sub.2                                                                               1 CHCH.sub.2 OMe                                                                          NH       NH      CO                                    1.306                                                                              CH.sub.2 1 CHMe     NCOMe    NCOMe   CO                                    1.307                                                                              CH.sub.2 1 CHMe     NCOCH.sub.2 OMe                                                                         NCOCH.sub.2 OMe                                                                        CO                                    1.308                                                                              CH.sub.2 1 CHMe     NCO-cPr  NCO-cPr CO                                    1.309                                                                              CH.sub.2 1 CHMe     NCOCH.sub.2 Cl                                                                          NCOCH.sub.2 Cl                                                                         CO                                    1.310                                                                              CH.sub.2 1 CHMe     NCOEt    NCOEt   CO                                    1.311                                                                              CH.sub.2 1 CHMe     NCOCHMe.sub.2                                                                           NCOCHMe.sub.2                                                                          CO                                    1.312                                                                              CH.sub.2 1 CHMe     NCOOEt   NCOOEt  CO                                    1.313                                                                              CH.sub.2 1 CHMe     NCOMe    NH      CO                                    1.314                                                                              CH.sub.2 1 CHMe     NCOCH.sub.2 OMe                                                                         NH      CO                                    1.315                                                                              CH.sub.2 1 CHMe     NCO-cPr  NH      CO                                    1.316                                                                              CH.sub.2 1 CHMe     NCOCH.sub.2 Cl                                                                          NH      CO                                    1.317                                                                              CH.sub.2 1 CHMe     NCOEt    NH      CO                                    1.318                                                                              CH.sub.2 1 CHMe     NCOCHMe.sub.2                                                                           NH      CO                                    1.319                                                                              CH.sub.2 1 CHMe     NCOOEt   NH      CO                                    1.320                                                                              CH       0          CMe      N(NCH-3-                                                                               CO                                                                     pyridinyl)                                    1.321                                                                              CH.sub.2 0          C(Me)(OH)                                                                               N(NCH-3-                                                                               CO                                                                     pyridinyl)                                    1.322                                                                              CH       0          N        NCONHMe CO                                    1.323                                                                              CH       0          N        NCOiPr  CO                                    1.324                                                                              CH       0          N        NCOOEt  CO                                    1.325                                                                              CH       0          N        NCOtBu  CO                                    1.326                                                                              CH.sub.2 1 CO       NH       NMe     CO                                    1.327                                                                              CO       0          CH.sub.2 NNHCOMe CO                                    1.328                                                                              CH.sub.2 0          C(OH)Me  NNHEt   CO                                    1.329                                                                              CMe      0          CH       NNH.sub.2                                                                              CO                                    1.330                                                                              CO       0          CHMe     NiPr    CO                                    1.331                                                                              CH.sub.2 1 C(CH.sub.2 OCOMe)                                                                       N        NH      CO                                    1.332                                                                              CO       1 CHMe     NH       NH      CO                                    1.333                                                                              CH.sub.2 1 C(Z1.sup.a)                                                                             N        NH      CO                                    1.334                                                                              CH.sub.2 1 C(Z2.sup.a)                                                                             N        NH      CO                                    1.335                                                                              CH.sub.2 1 C(CH.sub.2 OEt)                                                                         N        NH      CO                                    __________________________________________________________________________      .sup.a Z1: CH.sub.2 SC.sub.2 H.sub.4 COOMe; Z2: CH.sub.2 SC.sub.2 H.sub.4      COOH                                                                     

                  TABLE 1a                                                         ______________________________________                                         (melting points of compounds from Table 1)                                     Comp.                m.p.(°)                                            ______________________________________                                         1.019                205-207                                                   1.041                193-194                                                   1.046                172                                                       1.058                210-212                                                   1.063                170-172                                                   1.066                151-153                                                   1.072                189-195                                                   1.074                126-129                                                   1.075                124-126                                                   1.080                solid                                                     1.115                164-166                                                   1.116                181-182                                                   1.117                264-265                                                   1.121                177-179                                                   1.123                255-256                                                   1.125                128-130                                                   1.138                200-202                                                   1.273                208-210                                                   1.276                128-130                                                   1.291                235-237                                                   1.306                176-178                                                   1.307                127-129                                                   1.308                146-148                                                   1.313                185-186                                                   1.315                189-192                                                   1.320                172-174                                                   1.321                175-182                                                   1.322                207-208                                                   1.323                145-146                                                   1.324                165-166                                                   1.325                170-172                                                   1.326                217-220                                                   1.327                180-182                                                   1.328                102-117                                                   1.329                164-165                                                   1.330                resin                                                     1.331                190-200                                                   1.332                161-162                                                   1.333                118                                                       1.334                237                                                       1.335                156-158                                                   ______________________________________                                    

                                      TABLE 1b                                     __________________________________________________________________________      ##STR19##                                                                     Comp.                                                                              A        m B       D        E       G                                      __________________________________________________________________________     b.001                                                                              CS       0         NH       NH      CS                                     b.002                                                                              CS       0         NH       NH      CO                                     b.003                                                                              CO       1 CMe     N        NH      CS                                     b.004                                                                              CO       1 C(C.sub.2 H.sub.4 iPr)                                                                 N        NH      CS                                     b.005                                                                              CO       1 C(CH.sub.2 iPr)                                                                        N        NH      CS                                     b.006                                                                              CO       1 CtBu    N        NH      CS                                     b.007                                                                              CO       1 CtBu    N        NH      CO                                     b.008                                                                              CO       1 CcPr    N        NH      CS                                     b.009                                                                              CO       1 CcHex   N        NH      CS                                     b.010                                                                              CO       1 NCH.sub.2 -cHex                                                                        CO       NH      CO                                     b.011                                                                              CO       1 CH.sub.2                                                                               CO       NH      CO                                     b.012                                                                              CO       1 CH.sub.2                                                                               CH.sub.2 NH      CO                                     b.013                                                                              CO       1 CH.sub.2                                                                               CMe.sub.2                                                                               NH      CO                                     b.014                                                                              CO       1 CH      CMe      NH      CO                                     b.015                                                                              CO       1 CH      N        NH      CS                                     b.016                                                                              CO       1 CH      CCF.sub.3                                                                               NH      CNH                                    b.017                                                                              CO       1 CMe.sub.2                                                                              CO       NH      CO                                     b.018                                                                              CO       1 CMe.sub.2                                                                              CH.sub.2 NH      CO                                     b.019                                                                              CO       1 CMe     N        NH      CO                                     b.020                                                                              CO       1 CtBu    N        NC.sub.2 H.sub.4 F                                                                     CS                                     b.021                                                                              CO       1 CEt     N        NH      CS                                     b.022                                                                              CO       0         CO       NH      CO                                     b.023                                                                              CO       0         NH       NH      CO                                     b.024                                                                              CO       0         CH.sub.2 S       CS                                     b.025                                                                              CO       0         CHCH.sub.2 COOMe                                                                        NH      CS                                     b.026                                                                              CO       0         CHC.sub.2 H.sub.4 COOMe                                                                 NH      CS                                     b.027                                                                              CO       0         NH       NH      CO                                     b.028                                                                              CO       0         CMeCHCMe.sub.2                                                                          NH      CO                                     b.029                                                                              CO       0         CMeCH.sub.2 CMe.sub.2                                                                   NH      CO                                     b.030                                                                              CO       0         CH.sub.2 NH      CS                                     b.031                                                                              CO       0         CMe.sub.2                                                                               NH      CO                                     b.032                                                                              CH.sub.2 0         CO       NMe     CS                                     b.033                                                                              CH.sub.2 0         CO       NiPr    CS                                     b.034                                                                              CH.sub.2 0         CO       NEt     CS                                     b.035                                                                              CH.sub.2 0         CO       NH      CO                                     b.036                                                                              CH.sub.2 0         CO       NH      CS                                     b.037                                                                              CH.sub.2 1 CMe.sub.2                                                                              CO       NH      CO                                     b.038                                                                              CH.sub.2 0         CO       NH      CO                                     b.039                                                                              CH.sub.2 1 CH.sub.2                                                                               CO       NH      CO                                     b.040                                                                              CH.sub.2 0         CH.sub.2 O       CO                                     b.041                                                                              CH.sub.2 0         CH.sub.2 NH      CO                                     b.042                                                                              CH.sub.2 0         CH.sub.2 NH      CS                                     b.043                                                                              CH.sub.2 0         CH.sub.2 CH.sub.2                                                                               CO                                     b.044                                                                              CH.sub.2 0         CH.sub.2 NH      CO                                     b.045                                                                              CH.sub.2 0         CH.sub.2 NH      CO                                     b.046                                                                              CH.sub.2 1 CH.sub.2                                                                               CH.sub.2 NH      CO                                     b.047                                                                              CH.sub.2 1 CMe.sub.2                                                                              CH.sub.2 NH      CO                                     b.048                                                                              CH.sub.2 1 CMe.sub.2                                                                              CH.sub.2 NH      CO                                     b.049                                                                              CH.sub.2 1 C(OMe).sub.2                                                                           CH.sub.2 NH      CO                                     b.050                                                                              CH.sub.2 1 C(OEt).sub.2                                                                           CH.sub.2 NH      CO                                     b.051                                                                              CH.sub.2 1 C(CH.sub.2 OH).sub.2                                                                   CH.sub.2 NH      CO                                     b.052                                                                              CH.sub.2 1 CO      CH.sub.2 NH      CO                                     b.053                                                                              CH.sub.2 1 CHOH    CH.sub.2 NH      CO                                     b.054                                                                              CH.sub.2 1 O       CH.sub.2 NH      CO                                     b.055                                                                              CH.sub.2 1 NMe     CH.sub.2 NH      CO                                     b.056                                                                              CH.sub.2 0         CH.sub.2 NH      CO                                     b.057                                                                              CH.sub.2 0         CH.sub.2 NMe     CO                                     b.058                                                                              CH.sub.2 0         CH.sub.2 NCOMe   CO                                     b.059                                                                              CH.sub.2 0         CH.sub.2 NCOEt   CO                                     b.060                                                                              CH.sub.2 0         CH.sub.2 NCO-nPr CO                                     b.061                                                                              CH.sub.2 0         CH.sub.2 NCOCH.sub.2 OMe                                                                        CO                                     b.062                                                                              CH.sub.2 0         CH.sub.2 NCOCHMe.sub.2                                                                          CO                                     b.063                                                                              CH.sub.2 1 CH.sub.2                                                                               CH.sub.2 NH      CO                                     b.064                                                                              CH.sub.2 1 CH.sub.2                                                                               CH.sub.2 NH      CO                                     b.065                                                                              CH.sub.2 1 CH.sub.2                                                                               CH.sub.2 NMe     CO                                     b.066                                                                              CH.sub.2 1 CH.sub.2                                                                               CH.sub.2 NCOMe   CO                                     b.067                                                                              CH.sub.2 1 CH.sub.2                                                                               CH.sub.2 NCOEt   CO                                     b.068                                                                              CH.sub.2 1 CH.sub.2                                                                               CH.sub.2 NCO-nPr CO                                     b.069                                                                              CH.sub.2 1 CH.sub.2                                                                               CH.sub.2 NCOCH.sub.2 OMe                                                                        CO                                     b.070                                                                              CH.sub.2 1 CH.sub.2                                                                               CH.sub.2 NCOCHMe.sub.2                                                                          CO                                     b.071                                                                              CH.sub.2 1 CH      CH       NH      CO                                     b.072                                                                              CH.sub.2 0         CHMe     NH      CO                                     b.073                                                                              CH.sub.2 0         CHMe     NH      CO                                     b.074                                                                              CH.sub.2 0         CHMe     NMe     CO                                     b.075                                                                              CH.sub.2 0         CHMe     NCOMe   CO                                     b.076                                                                              CH.sub.2 0         CHMe     NCOEt   CO                                     b.077                                                                              CH.sub.2 0         CHMe     NCO-nPr CO                                     b.078                                                                              CH.sub.2 0         CHMe     NCOCH.sub.2 OMe                                                                        CO                                     b.079                                                                              CH.sub.2 0         CHMe     NCOCHMe.sub.2                                                                          CO                                     b.080                                                                              CH.sub.2 1 CH.sub.2                                                                               CHMe     NH      CO                                     b.081                                                                              CH.sub.2 1 CH.sub.2                                                                               CHMe     NH      CO                                     b.082                                                                              CH.sub.2 1 CH.sub.2                                                                               CHMe     NMe     CO                                     b.083                                                                              CH.sub.2 1 CH.sub.2                                                                               CHMe     NCOMe   CO                                     b.084                                                                              CH.sub.2 1 CH.sub.2                                                                               CHMe     NCOEt   CO                                     b.085                                                                              CH.sub.2 1 CH.sub.2                                                                               CHMe     NCO-nPr CO                                     b.086                                                                              CH.sub.2 1 CH.sub.2                                                                               CHMe     NCOCH.sub.2 OMe                                                                        CO                                     b.087                                                                              CH.sub.2 1 CH.sub.2                                                                               CHMe     NCOCHMe.sub.2                                                                          CO                                     b.088                                                                              CH.sub.2 0         CHCH.sub.2 OMe                                                                          NH      CO                                     b.089                                                                              CH.sub.2 1 CH.sub.2                                                                               CHCH.sub.2 OMe                                                                          NH      CO                                     b.090                                                                              CH.sub.2 0         CH-tBu   NH      CO                                     b.091                                                                              CH.sub.2 1 CH.sub.2                                                                               CH-tBu   NH      CO                                     b.092                                                                              CH.sub.2 0         CH-iPr   NH      CO                                     b.093                                                                              CH.sub.2 1 CH.sub.2                                                                               CH-iPr   NH      CO                                     b.094                                                                              CH.sub.2 0         CH-cPr   NH      CO                                     b.095                                                                              CH.sub.2 1 CH.sub.2                                                                               CH-cPr   NH      CO                                     b.096                                                                              CH.sub.2 0         CHEt     NH      CO                                     b.098                                                                              CH.sub.2 0         CHEt     NMe     CO                                     b.099                                                                              CH.sub.2 0         CHEt     NCOMe   CO                                     b.100                                                                              CH.sub.2 0         CHEt     NCOEt   CO                                     b.101                                                                              CH.sub.2 0         CHEt     NCO-nPr CO                                     b.102                                                                              CH.sub.2 0         CHEt     NCOCH.sub.2 OMe                                                                        CO                                     b.103                                                                              CH.sub.2 0         CHEt     NCOCHMe.sub.2                                                                          CO                                     b.104                                                                              CH.sub.2 1 CH.sub.2                                                                               CHEt     NH      CO                                     b.106                                                                              CH.sub.2 1 CH.sub.2                                                                               CHEt     NMe     CO                                     b.107                                                                              CH.sub.2 1 CH.sub.2                                                                               CHEt     NCOMe   CO                                     b.108                                                                              CH.sub.2 1 CH.sub.2                                                                               CHEt     NCOEt   CO                                     b.109                                                                              CH.sub.2 1 CH.sub.2                                                                               CHEt     NCO-nPr CO                                     b.110                                                                              CH.sub.2 1 CH.sub.2                                                                               CHEt     NCOCH.sub.2 OMe                                                                        CO                                     b.111                                                                              CH.sub.2 1 CH.sub.2                                                                               CHEt     NCOCHMe.sub.2                                                                          CO                                     b.112                                                                              CH.sub.2 1 CMe     CH       NH      CO                                     b.113                                                                              CH.sub.2 1 CEt     CH       NH      CO                                     b.114                                                                              CH.sub.2 1 CH      C(t-Bu)  NMe     CO                                     b.115                                                                              CH       0         N        NCOCH.sub.3                                                                            CO                                     b.116                                                                              CH       0         N        NCONMe.sub.2                                                                           CNH                                    b.117                                                                              CH       0         N        NH      CO                                     b.118                                                                              CH       1 CH      NH       NH      CO                                     b.119                                                                              CH       1 CMe     CH.sub.2 NH      CO                                     b.120                                                                              CH       1 CEt     CH.sub.2 NH      CO                                     b.121                                                                              CH       0         CMe      NH      CO                                     b.122                                                                              CH       1 CH      CHMe     NH      CO                                     b.123                                                                              CH       0         CtBu     NH      CO                                     b.124                                                                              CHMe     0         CH.sub.2 NH      CO                                     b.125                                                                              CHMe     0         CH.sub.2 NMe     CO                                     b.126                                                                              CHMe     0         CH.sub.2 NCOMe   CO                                     b.127                                                                              CHMe     0         CH.sub.2 NCOEt   CO                                     b.128                                                                              CHMe     0         CH.sub.2 NCOnPr  CO                                     b.129                                                                              CHMe     0         CH.sub.2 NCOCH.sub.2 OMe                                                                        CO                                     b.130                                                                              CHMe     0         CH.sub.2 NCOCHMe.sub.2                                                                          CO                                     b.131                                                                              CHMe     1 CH.sub.2                                                                               CH.sub.2 NH      CO                                     b.132                                                                              CHMe     1 CH.sub.2                                                                               CH.sub.2 NMe     CO                                     b.133                                                                              CHMe     1 CH.sub.2                                                                               CH.sub.2 NCOMe   CO                                     b.134                                                                              CHMe     1 CH.sub.2                                                                               CH.sub.2 NCOEt   CO                                     b.135                                                                              CHMe     1 CH.sub.2                                                                               CH.sub.2 NCOnPr  CO                                     b.136                                                                              CHMe     1 CH.sub.2                                                                               CH.sub.2 NCOCH.sub.2 OMe                                                                        CO                                     b.137                                                                              CHMe     1 CH.sub.2                                                                               CH.sub.2 NCOCHMe.sub.2                                                                          CO                                     b.138                                                                              CMe      0         C        NCH.sub.3                                                                              CO                                     b.139                                                                              CHMe     1 CH      CH       NH      CO                                     b.140                                                                              CHMe     0         CHMe     NH      CO                                     b.141                                                                              CHMe     0         CHMe     NMe     CO                                     b.142                                                                              CHMe     0         CHMe     NCOMe   CO                                     b.143                                                                              CHMe     0         CHMe     NCOEt   CO                                     b.144                                                                              CHMe     0         CHMe     NCOnPr  CO                                     b.145                                                                              CHMe     0         CHMe     NCOCH.sub.2 OMe                                                                        CO                                     b.146                                                                              CHMe     0         CHMe     NCOCHMe.sub.2                                                                          CO                                     b.147                                                                              CHMe     1 CH.sub.2                                                                               CHMe     NH      CO                                     b.148                                                                              CHMe     1 CH.sub.2                                                                               CHMe     NMe     CO                                     b.149                                                                              CHMe     1 CH.sub.2                                                                               CHMe     NCOMe   CO                                     b.150                                                                              CHMe     1 CH.sub.2                                                                               CHMe     NCOEt   CO                                     b.151                                                                              CHMe     1 CH.sub.2                                                                               CHMe     NCOnPr  CO                                     b.152                                                                              CHMe     1 CH.sub.2                                                                               CHMe     NCOCH.sub.2 OMe                                                                        CO                                     b.153                                                                              CHMe     1 CH.sub.2                                                                               CHMe     NCOCHMe.sub.2                                                                          CO                                     b.154                                                                              CHMe     0         CHEt     NH      CO                                     b.155                                                                              CHMe     0         CHEt     NMe     CO                                     b.156                                                                              CHMe     0         CHEt     NCOMe   CO                                     b.157                                                                              CHMe     0         CHEt     NCOEt   CO                                     b.158                                                                              CHMe     0         CHEt     NCOnPr  CO                                     b.159                                                                              CHMe     0         CHEt     NCOCH.sub.2 OMe                                                                        CO                                     b.160                                                                              CHMe     0         CHEt     NCOCHMe.sub.2                                                                          CO                                     b.161                                                                              CHMe     1 CH.sub.2                                                                               CHEt     NH      CO                                     b.162                                                                              CHMe     1 CH.sub.2                                                                               CHEt     NMe     CO                                     b.163                                                                              CHMe     1 CH.sub.2                                                                               CHEt     NCOMe   CO                                     b.164                                                                              CHMe     1 CH.sub.2                                                                               CHEt     NCOEt   CO                                     b.165                                                                              CHMe     1 CH.sub.2                                                                               CHEt     NCOnPr  CO                                     b.166                                                                              CHMe     1 CH.sub.2                                                                               CHEt     NCOCH.sub.2 OMe                                                                        CO                                     b.167                                                                              CHMe     1 CH.sub.2                                                                               CHEt     NCOCHMe.sub.2                                                                          CO                                     b.168                                                                              CHCH.sub.2 OMe                                                                          0         CH.sub.2 NH      CO                                     b.169                                                                              CHCH.sub.2 OMe                                                                          1 CH.sub.2                                                                               CH.sub.2 NH      CO                                     b.170                                                                              CHtBu    0         CH.sub.2 NH      CO                                     b.171                                                                              CHtBu    1 CH.sub.2                                                                               CH.sub.2 NH      CO                                     b.172                                                                              CHiPr    0         CH.sub.2 NH      CO                                     b.173                                                                              CHiPr    1 CH.sub.2                                                                               CH.sub.2 NH      CO                                     b.174                                                                              CHiPr    0         CH.sub.2 NH      CO                                     b.175                                                                              CHiPr    0         CH.sub.2 NMe     CO                                     b.176                                                                              CHiPr    0         CH.sub.2 NCOMe   CO                                     b.177                                                                              CHiPr    0         CH.sub.2 NCOEt   CO                                     b.178                                                                              CHiPr    0         CH.sub.2 NCOnPr  CO                                     b.179                                                                              CHiPr    0         CH.sub.2 NCOCH.sub.2 OMe                                                                        CO                                     b.180                                                                              CHiPr    0         CH.sub.2 NCOCHMe.sub.2                                                                          CO                                     b.181                                                                              CHiPr    1 CH.sub.2                                                                               CH.sub.2 NH      CO                                     b.182                                                                              CHiPr    1 CH.sub.2                                                                               CH.sub.2 NMe     CO                                     b.183                                                                              CHiPr    1 CH.sub.2                                                                               CH.sub.2 NCOMe   CO                                     b.184                                                                              CHiPr    1 CH.sub.2                                                                               CH.sub.2 NCOEt   CO                                     b.185                                                                              CHiPr    1 CH.sub.2                                                                               CH.sub.2 NCO-nPr CO                                     b.186                                                                              CHiPr    1 CH.sub.2                                                                               CH.sub.2 NCOCH.sub.2 OMe                                                                        CO                                     b.187                                                                              CHiPr    1 CH.sub.2                                                                               CH.sub.2 NCOCHMe.sub.2                                                                          CO                                     b.188                                                                              CHiPr    0         CHMe     NH      CO                                     b.189                                                                              CHiPr    0         CHMe     NMe     CO                                     b.190                                                                              CHiPr    0         CHMe     NCOMe   CO                                     b.191                                                                              CHiPr    0         CHMe     NCOEt   CO                                     b.192                                                                              CHiPr    0         CHMe     NCOnPr  CO                                     b.193                                                                              CHiPr    0         CHMe     NCOCH.sub.2 OMe                                                                        CO                                     b.194                                                                              CHiPr    0         CHMe     NCOCHMe.sub.2                                                                          CO                                     b.195                                                                              CHiPr    1 CH.sub.2                                                                               CHMe     NH      CO                                     b.196                                                                              CHiPr    1 CH.sub.2                                                                               CHMe     NMe     CO                                     b.197                                                                              CHiPr    1 CH.sub.2                                                                               CHMe     NCOMe   CO                                     b.198                                                                              CHiPr    1 CH.sub.2                                                                               CHMe     NCOEt   CO                                     b.199                                                                              CHiPr    1 CH.sub.2                                                                               CHMe     NCOnPr  CO                                     b.200                                                                              CHiPr    1 CH.sub.2                                                                               CHMe     NCOCH.sub.2 OMe                                                                        CO                                     b.201                                                                              CHiPr    1 CH.sub.2                                                                               CHMe     NCOCHMe.sub.2                                                                          CO                                     b.202                                                                              CHiPr    0         CHEt     NH      CO                                     b.203                                                                              CHiPr    0         CHEt     NMe     CO                                     b.204                                                                              CHiPr    0         CHEt     NCOMe   CO                                     b.205                                                                              CHiPr    0         CHEt     NCOEt   CO                                     b.206                                                                              CHiPr    0         CHEt     NCOnPr  CO                                     b.207                                                                              CHiPr    0         CHEt     NCOCH.sub.2 OMe                                                                        CO                                     b.208                                                                              CHiPr    0         CHEt     NCOCHMe.sub.2                                                                          CO                                     b.209                                                                              CHiPr    1 CH.sub.2                                                                               CHEt     NH      CO                                     b.210                                                                              CHiPr    1 CH.sub.2                                                                               CHEt     NMe     CO                                     b.211                                                                              CHiPr    1 CH.sub.2                                                                               CHEt     NCOMe   CO                                     b.212                                                                              CHiPr    1 CH.sub.2                                                                               CHEt     NCOEt   CO                                     b.213                                                                              CHiPr    1 CH.sub.2                                                                               CHEt     NCOnPr  CO                                     b.214                                                                              CHiPr    1 CH.sub.2                                                                               CHEt     NCOCH.sub.2 OMe                                                                        CO                                     b.215                                                                              CHiPr    1 CH.sub.2                                                                               CHEt     NCOCHMe.sub.2                                                                          CO                                     b.216                                                                              CHcPr    0         CH.sub.2 NH      CO                                     b.217                                                                              CHcPr    1 CH.sub.2                                                                               CH.sub.2 NH      CO                                     b.218                                                                              CHEt     0         CH.sub.2 NH      CO                                     b.219                                                                              CHEt     1 CH.sub.2                                                                               CH.sub.2 NH      CO                                     b.220                                                                              CHEt     0         CH.sub.2 NH      CO                                     b.221                                                                              CHEt     0         CH.sub.2 NMe     CO                                     b.222                                                                              CHEt     0         CH.sub.2 NCOMe   CO                                     b.223                                                                              CHEt     0         CH.sub.2 NCOEt   CO                                     b.224                                                                              CHEt     0         CH.sub.2 NCOnPr  CO                                     b.225                                                                              CHEt     0         CH.sub.2 NCOCH.sub.2 OMe                                                                        CO                                     b.226                                                                              CHEt     0         CH.sub.2 NCOCHMe.sub.2                                                                          CO                                     b.227                                                                              CHEt     1 CH.sub.2                                                                               CH.sub.2 NH      CO                                     b.228                                                                              CHEt     1 CH.sub.2                                                                               CH.sub.2 NMe     CO                                     b.229                                                                              CHEt     1 CH.sub.2                                                                               CH.sub.2 NCOMe   CO                                     b.230                                                                              CHEt     1 CH.sub.2                                                                               CH.sub.2 NCOEt   CO                                     b.231                                                                              CHEt     1 CH.sub.2                                                                               CH.sub.2 NCOnPr  CO                                     b.232                                                                              CHEt     1 CH.sub.2                                                                               CH.sub.2 NCOCH.sub.2 OMe                                                                        CO                                     b.223                                                                              CHEt     1 CH.sub.2                                                                               CH.sub.2 NCOCHMe.sub.2                                                                          CO                                     b.234                                                                              CHEt     0         CHMe     NH      CO                                     b.235                                                                              CHEt     0         CHMe     NMe     CO                                     b.236                                                                              CHEt     0         CHMe     NCOMe   CO                                     b.237                                                                              CHEt     0         CHMe     NCOEt   CO                                     b.238                                                                              CHEt     0         CHMe     NCO-nPr CO                                     b.239                                                                              CHEt     0         CHMe     NCOCH.sub.2 OMe                                                                        CO                                     b.240                                                                              CHEt     0         CHMe     NCOCH.sub.2 Me.sub.2                                                                   CO                                     b.241                                                                              CHEt     1 CH.sub.2                                                                               CHMe     NH      CO                                     b.242                                                                              CHEt     1 CH.sub.2                                                                               CHMe     NMe     CO                                     b.243                                                                              CHEt     1 CH.sub.2                                                                               CHMe     NCOMe   CO                                     b.244                                                                              CHEt     1 CH.sub.2                                                                               CHMe     NCOEt   CO                                     b.245                                                                              CHEt     1 CH.sub.2                                                                               CHMe     NCOnPr  CO                                     b.246                                                                              CHEt     1 CH.sub.2                                                                               CHMe     NCOCH.sub.2 OMe                                                                        CO                                     b.247                                                                              CHEt     1 CH.sub.2                                                                               CHMe     NCOCHMe.sub.2                                                                          CO                                     b.248                                                                              CHEt     0         CHEt     NH      CO                                     b.249                                                                              CHEt     0         CHEt     NMe     CO                                     b.250                                                                              CHEt     0         CHEt     NCOMe   CO                                     b.251                                                                              CHEt     0         CHEt     NCOEt   CO                                     b.252                                                                              CHEt     0         CHEt     NCOnPr  CO                                     b.253                                                                              CHEt     0         CHEt     NCOCH.sub.2 OMe                                                                        CO                                     b.254                                                                              CHEt     0         CHEt     NCOCHMe.sub.2                                                                          CO                                     b.255                                                                              CHEt     1 CH.sub.2                                                                               CHEt     NH      CO                                     b.256                                                                              CHEt     1 CH.sub.2                                                                               CHEt     NMe     CO                                     b.257                                                                              CHEt     1 CH.sub.2                                                                               CHEt     NCOMe   CO                                     b.258                                                                              CHEt     1 CH.sub.2                                                                               CHEt     NCOEt   CO                                     b.259                                                                              CHEt     1 CH.sub.2                                                                               CHEt     NCOnPr  CO                                     b.260                                                                              CHEt     1 CH.sub.2                                                                               CHEt     NCOCH.sub.2 OMe                                                                        CO                                     b.261                                                                              CHEt     1 CH.sub.2                                                                               CHEt     NCOCHMe.sub.2                                                                          CO                                     b.262                                                                              CSMe     1 N       CO       NMe     CO                                     b.263                                                                              CNHCOOEt 0         N        NH      CS                                     b.264                                                                              CNHCOOMe 0         N        NH      CS                                     b.265                                                                              CNHMe    1 N       CO       NMe     CO                                     b.266                                                                              CMe.sub.2                                                                               0         CO       NH      CO                                     b.267                                                                              CMe.sub.2                                                                               1 CH.sub.2                                                                               CO       NH      CO                                     b.268                                                                              CMe.sub.2                                                                               0         CH.sub.2 NH      CO                                     b.269                                                                              CMe.sub.2                                                                               1 CH.sub.2                                                                               CH.sub.2 NH      CO                                     b.270                                                                              CMe      0         CCOOEt   S       CNH                                    b.271                                                                              CMe      0         N        NH      CS                                     b.273                                                                              CMe      0         N        NH      CO                                     b.274                                                                              CMe      1 CH      NH       NH      CO                                     b.275                                                                              CMe      0         CH       S       CNH                                    b.276                                                                              CHMe     0         CH.sub.2 NH      CO                                     b.277                                                                              CMe      1 CH      CH.sub.2 NH      CO                                     b.278                                                                              CCH.sub.2 OMe                                                                           0         N        NH      CS                                     b.279                                                                              CCH.sub.2 OEt                                                                           0         N        NH      CS                                     b.280                                                                              CCH.sub.2 iPr                                                                           0         N        NH      CS                                     b.281                                                                              CCF.sub.3                                                                               0         N        NH      CS                                     b.282                                                                              CcHex    0         N        NH      CS                                     b.283                                                                              CiPr     0         N        NH      CS                                     b.284                                                                              CcPr     0         N        NH      CS                                     b.285                                                                              CEt      0         N        NH      CS                                     b.286                                                                              CEt      0         N        NH      CO                                     b.287                                                                              CC.sub.2 F.sub.5                                                                        0         N        NH      CS                                     b.288                                                                              CBr      0         N        NH      CS                                     b.289                                                                              C(NH)    0         CMe.sub.2                                                                               NH      CO                                     b.290                                                                              C(NH)    1 CH      CMe      NH      CO                                     b.291                                                                              CH.sub.2 1 CHMe    NH       NH      CO                                     b.292                                                                              CH.sub.2 1 CHEt    NH       NH      CO                                     b.293                                                                              CH.sub.2 1 CHcPr   NH       NH      CO                                     b.294                                                                              CH.sub.2 1 CHtBu   NH       NH      CO                                     b.295                                                                              CH.sub.2 1 CHCH.sub.2 OMe                                                                         NH       NH      CO                                     b.296                                                                              CHMe     1 CHMe    NH       NH      CO                                     b.297                                                                              CHMe     1 CHEt    NH       NH      CO                                     b.298                                                                              CHMe     1 CHcPr   NH       NH      CO                                     b.299                                                                              CHMe     1 CHtBu   NH       NH      CO                                     b.300                                                                              CHMe     1 CHCH.sub.2 OMe                                                                         NH       NH      CO                                     b.301                                                                              CMe.sub.2                                                                               1 CHMe    NH       NH      CO                                     b.302                                                                              CMe.sub.2                                                                               1 CHEt    NH       NH      CO                                     b.303                                                                              CMe.sub.2                                                                               1 CHcPr   NH       NH      CO                                     b.304                                                                              CMe.sub.2                                                                               1 CHtBu   NH       NH      CO                                     b.305                                                                              CMe.sub.2                                                                               1 CHCH.sub.2 OMe                                                                         NH       NH      CO                                     b.306                                                                              CH.sub.2 1 CHMe    NCOMe    NCOMe   CO                                     b.307                                                                              CH.sub.2 1 CHMe    NCOCH.sub.2 OMe                                                                         NCOCH.sub.2 OMe                                                                        CO                                     b.308                                                                              CH.sub.2 1 CHMe    NCOiPr   NCOiPr  CO                                     b.309                                                                              CH.sub.2 1 CHMe    NCOCH.sub.2 Cl                                                                          NCOCH.sub.2 Cl                                                                         CO                                     b.310                                                                              CH.sub.2 1 CHMe    NCOEt    NCOEt   CO                                     b.311                                                                              CH.sub.2 1 CHMe    NCOCHMe.sub.2                                                                           NCOCHMe.sub.2                                                                          CO                                     b.312                                                                              CH.sub.2 1 CHMe    NCOOEt   NCOOEt  CO                                     b.313                                                                              CH.sub.2 1 CHMe    NCOMe    NH      CO                                     b.314                                                                              CH.sub.2 1 CHMe    NCOCH.sub.2 OMe                                                                         NH      CO                                     b.315                                                                              CH.sub.2 1 CHMe    NCO-cPr  NH      CO                                     b.316                                                                              CH.sub.2 1 CHMe    NCOCH.sub.2 Cl                                                                          NH      CO                                     b.317                                                                              CH.sub.2 1 CHMe    NCOEt    NH      CO                                     b.318                                                                              CH.sub.2 1 CHMe    NCOCHMe.sub.2                                                                           NH      CO                                     b.319                                                                              CH.sub.2 1 CHMe    NCOOEt   NH      CO                                     b.320                                                                              CH       0         CMe      N(NCH-3-                                                                               CO                                                                     pyridinyl)                                     b.321                                                                              CH.sub.2 0         C(Me)(OH)                                                                               N(NCH-3-                                                                               CO                                                                     pyridinyl)                                     __________________________________________________________________________

                  TABLE 1c                                                         ______________________________________                                         (melting points of compounds from Table 1b)                                    Comp.                m.p.(°)                                            ______________________________________                                         b.072                218-221                                                   b.074                223-225                                                   b.080                207-213                                                   b.083                270-275                                                   b.124                190-195                                                   b.273                >260                                                      ______________________________________                                    

EXAMPLE P11 4-Amino-1,2,4-triazol-3-one (Compound 2.117 in Table 2)

A mixture of 54 g of carbohydrazide and 88.8 g of orthoformic acid triethyl ester is maintained at 130° for 4 hours, the alcohol that forms being distilled off continuously. The resulting solid residue is recrystallised twice from 200 ml of ethanol/water (3:1). 32.5 g of the title compound having a melting point of 186°-188° are obtained.

EXAMPLE P12 4-Amino-5-methyl-1,2,4-triazol-3-one (Compound 2.272 in Table 2)

A mixture of 52.2 g of carbethoxyhydrazone and 22.5 g of hydrazine hydrate in 200 ml of n-propanol is stirred under reflux for 30 hours. The mixture is cooled and then the crystals are filtered off with suction, washed with a small amount of n-propanol and dried under a high vacuum. 17.4 g of the title compound having a melting point of 225°-230° are obtained.

EXAMPLE P13 1-Amino-3,4-dimethyl-1,3-dihydroimidazol-2-one (Compound 2.121 in Table 2)

2 g of hydrazine hydrate are added to a solution of 2 g of 3,4-dimethyl-1-(pyridin-3-ylmethyleneamino)-2,3-dihydroimidazol-2-one in 12 ml of methanol and the suspension is boiled under reflux for 6 hours, then concentrated by evaporation and chromatographed on silica gel. 1 g of pyridine-3-carbaldehyde hydrazone and 0.7 g of the title compound having a melting point of 115°-119° are thus obtained.

EXAMPLE P14 1-Amino-3,4-dimethylimidazolidin-2-one (Compound 2.074 in Table 2)

1.6 g of Rh/C are added to a solution of 1-amino-3,4-dimethyl-2-oxo-1,3-dihydroimidazole hydrochloride in 150 ml of methanol and the reaction mixture is hydrogenated with hydrogen under normal pressure. After 4 hours, 1.13 litres of hydrogen have been taken up and the reaction ceases. The reaction mixture is then filtered over Celite and concentrated by evaporation. The residue is stirred with tetrahydrofuran. The crystals are filtered off with suction and dried in vacuo at 60°. 7 g of the title compound in the form of the hydrochloride having a melting point of 162°-164° are obtained.

EXAMPLE P15 1-Amino-3,4-dimethyl-2-oxo-1,3-dihydroimidazole hydrochloride (Compound 2.121 in Table 2 in the form of the hydrochloride)

80.8 g of (3,4-dimethyl-2-oxo-1,3-dihydroimidazol-1-yl) acetamide are suspended in 800 ml of methanol and then heated to 42°. At that temperature, 28 g of hydrogen chloride gas are introduced in the course of 40 minutes; with heating to more than 50° a clear solution forms. The clear solution is concentrated and the residue is stirred with a small amount of tetrahydrofuran. The crystals that have precipitated are filtered off with suction and dried. The hydrochloride of the title compound having a melting point of 162°-165° is thus obtained.

EXAMPLE P16 4-Amino-6-methyl-3-oxo-1,4,5,6-tetrahydro-1,2,4-triazine hydrochloride (Compound 2.291 in Table 2 in the form of the hydrochloride)

0.4 g of platinum oxide is added to a solution of 4-amino-6-methyl-3-oxo-4,5-dihydro-1,2,4-triazine hydrochloride in 80 ml of methanol and 8 ml of water, and then in the course of 200 minutes 614 ml of hydrogen are introduced. The catalyst is filtered off and the filtrate is concentrated by evaporation. The residue is concentrated by evaporation several times with 20 ml of isopropanol and 20 ml of toluene each time and then stirred with ether. 3.8 g of the title compound are thus obtained.

EXAMPLE P17

The other compounds listed in Tables 2 and 2a can also be prepared in a manner analogous to that described in Examples P11 to P16. Some of the examples listed in Table 2 are obtained via the compounds listed in Table 3 (in accordance with Preparation Variant e), 3a (in accordance with Preparation Variant g), 7 (in accordance with Preparation Variant p), 8a/b (in accordance with Preparation Variant n) and 9 (in accordance with Preparation Variant i).

                                      TABLE 2                                      __________________________________________________________________________      ##STR20##                                                                     Comp.                                                                              A        m B       D        E        G                                     __________________________________________________________________________     2.001                                                                              CS       0         NH       NH       CS                                    2.002                                                                              CS       0         NH       NH       CO                                    2.003                                                                              CO       1 CMe     N        NH       CS                                    2.004                                                                              CO       1 C(C.sub.2 H.sub.4 iPr)                                                                 N        NH       CS                                    2.005                                                                              CO       1 C(CH.sub.2 iPr)                                                                        N        NH       CS                                    2.006                                                                              CO       1 CtBu    N        NH       CS                                    2.007                                                                              CO       1 CtBu    N        NH       CO                                    2.008                                                                              CO       1 CcPr    N        NH       CS                                    2.009                                                                              CO       1 CcHex   N        NH       CS                                    2.010                                                                              CO       1 NCH.sub.2 -cHex                                                                        CO       NH       CO                                    2.011                                                                              CO       1 CH.sub.2                                                                               CO       NH       CO                                    2.012                                                                              CO       1 CH.sub.2                                                                               CH.sub.2 NH       CO                                    2.013                                                                              CO       1 CH.sub.2                                                                               CMe.sub.2                                                                               NH       CO                                    2.014                                                                              CO       1 CH      CMe      NH       CO                                    2.015                                                                              CO       1 CH      N        NH       CS                                    2.016                                                                              CO       1 CH      C(CF.sub.3)                                                                             NH       CNH                                   2.017                                                                              CO       1 CMe.sub.2                                                                              CO       NH       CO                                    2.018                                                                              CO       1 CMe.sub.2                                                                              CH.sub.2 NH       CO                                    2.019                                                                              CO       1 CMe     N        NH       CO                                    2.020                                                                              CO       1 CtBu    N        NC.sub.2 H.sub.4 F                                                                      CS                                    2.021                                                                              CO       1 CEt     N        NH       CS                                    2.022                                                                              CO       0         CO       NH       CO                                    2.023                                                                              CO       0         NH       NH       CO                                    2.024                                                                              CO       0         CH.sub.2 S        CS                                    2.025                                                                              CO       0         CHCH.sub.2 COOMe                                                                        NH       CS                                    2.026                                                                              CO       0         CHC.sub.2 H.sub.4 COOMe                                                                 NH       CS                                    2.027                                                                              CO       0         NH       NH       CO                                    2.028                                                                              CO       0         CMeCHCMe.sub.2                                                                          NH       CO                                    2.029                                                                              CO       0         CMeCH.sub.2 CMe.sub.2                                                                   NH       CO                                    2.030                                                                              CO       0         CH.sub.2 NH       CS                                    2.030                                                                              CO       0         CH.sub.2 NH       CS                                    2.031                                                                              CO       0         CMe.sub.2                                                                               NH       CO                                    2.032                                                                              CH.sub.2 0         CO       NMe      CS                                    2.033                                                                              CH.sub.2 0         CO       NiPr     CS                                    2.034                                                                              CH.sub.2 0         CO       NEt      CS                                    2.035                                                                              CH.sub.2 0         CO       NH       CO                                    2.036                                                                              CH.sub.2 0         CO       NH       CS                                    2.037                                                                              CH.sub.2 1 CMe.sub.2                                                                              CO       NH       CO                                    2.038                                                                              CH.sub.2 0         CO       NH       CO                                    2.039                                                                              CH.sub.2 1 CH.sub.2                                                                               CO       NH       CO                                    2.040                                                                              CH.sub.2 0         CH.sub.2 O        CO                                    2.041                                                                              CH.sub.2 0         CH.sub.2 NH       CO                                    2.042                                                                              CH.sub.2 0         CH.sub.2 NH       CS                                    2.043                                                                              CH.sub.2 0         CH.sub.2 CH.sub.2 CO                                    2.044                                                                              CH.sub.2 0         CH.sub.2 NH       CO                                    2.045                                                                              CH.sub.2 0         CH.sub.2 NH       CO                                    2.046                                                                              CH.sub.2 1 CH.sub.2                                                                               CH.sub.2 NH       CO                                    2.047                                                                              CH.sub.2 1 CMe.sub.2                                                                              CH.sub.2 NH       CO                                    2.048                                                                              CH.sub.2 1 CMe.sub.2                                                                              CH.sub.2 NH       CO                                    2.049                                                                              CH.sub.2 1 C(OMe).sub.2                                                                           CH.sub.2 NH       CO                                    2.050                                                                              CH.sub.2 1 C(OEt).sub.2                                                                           CH.sub.2 NH       CO                                    2.051                                                                              CH.sub.2 1 C(CH.sub.2 OH).sub.2                                                                   CH.sub.2 NH       CO                                    2.052                                                                              CH.sub.2 1 CO      CH.sub.2 NH       CO                                    2.053                                                                              CH.sub.2 1 CHOH    CH.sub.2 NH       CO                                    2.054                                                                              CH.sub.2 1 O       CH.sub.2 NH       CO                                    2.055                                                                              CH.sub.2 1 NMe     CH.sub.2 NH       CO                                    2.056                                                                              CH.sub.2 0         CH.sub.2 NH       CO                                    2.057                                                                              CH.sub.2 0         CH.sub.2 NMe      CO                                    2.058                                                                              CH.sub.2 0         CH.sub.2 NCOMe    CO                                    2.059                                                                              CH.sub.2 0         CH.sub.2 NCOEt    CO                                    2.060                                                                              CH.sub.2 0         CH.sub.2 NCOnPr   CO                                    2.061                                                                              CH.sub.2 0         CH.sub.2 NCOCH.sub.2 OMe                                                                         CO                                    2.062                                                                              CH.sub.2 0         CH.sub.2 NCOCHMe.sub.2                                                                           CO                                    2.063                                                                              CH.sub.2 1 CH.sub.2                                                                               CH.sub.2 NH       CO                                    2.064                                                                              CH.sub.2 1 CH.sub.2                                                                               CH.sub.2 NH       CO                                    2.065                                                                              CH.sub.2 1 CH.sub.2                                                                               CH.sub.2 NMe      CO                                    2.066                                                                              CH.sub.2 1 CH.sub.2                                                                               CH.sub.2 NCOMe    CO                                    2.067                                                                              CH.sub.2 1 CH.sub.2                                                                               CH.sub.2 NCOEt    CO                                    2.068                                                                              CH.sub.2 1 CH.sub.2                                                                               CH.sub.2 NCOnPr   CO                                    2.069                                                                              CH.sub.2 1 CH.sub.2                                                                               CH.sub.2 NCOCH.sub.2 OMe                                                                         CO                                    2.070                                                                              CH.sub.2 1 CH.sub.2                                                                               CH.sub.2 NCOCHMe.sub.2                                                                           CO                                    2.071                                                                              CH.sub.2 1 CH      CH       NH       CO                                    2.072                                                                              CH.sub.2 0         CHMe     NH       CO                                    2.073                                                                              CH.sub.2 0         CHMe     NH       CO                                    2.074                                                                              CH.sub.2 0         CHMe     NMe      CO                                    2.075                                                                              CH.sub.2 0         CHMe     NCOMe    CO                                    2.076                                                                              CH.sub.2 0         CHMe     NCOEt    CO                                    2.077                                                                              CH.sub.2 0         CHMe     NCOnPr   CO                                    2.078                                                                              CH.sub.2 0         CHMe     NCOCH.sub.2 OMe                                                                         CO                                    2.079                                                                              CH.sub.2 0         CHMe     NCOCHMe.sub.2                                                                           CO                                    2.080                                                                              CH.sub.2 1 CH.sub.2                                                                               CHMe     NH       CO                                    2.081                                                                              CH.sub.2 1 CH.sub.2                                                                               CHMe     NH       CO                                    2.082                                                                              CH.sub.2 1 CH.sub.2                                                                               CHMe     NMe      CO                                    2.083                                                                              CH.sub.2 1 CH.sub.2                                                                               CHMe     NCOMe    CO                                    2.084                                                                              CH.sub.2 1 CH.sub.2                                                                               CHMe     NCOEt    CO                                    2.085                                                                              CH.sub.2 1 CH.sub.2                                                                               CHMe     NCOnPr   CO                                    2.086                                                                              CH.sub.2 1 CH.sub.2                                                                               CHMe     NCOCH.sub.2 OMe                                                                         CO                                    2.087                                                                              CH.sub.2 1 CH.sub.2                                                                               CHMe     NCOCHMe.sub.2                                                                           CO                                    2.088                                                                              CH.sub.2 0         CHCH.sub.2 OMe                                                                          NH       CO                                    2.089                                                                              CH.sub.2 1 CH.sub.2                                                                               CHCH.sub.2 OMe                                                                          NH       CO                                    2.090                                                                              CH.sub.2 0         CHtBu    NH       CO                                    2.091                                                                              CH.sub.2 1 CH.sub.2                                                                               CHtBu    NH       CO                                    2.092                                                                              CH.sub.2 0         CHiPr    NH       CO                                    2.093                                                                              CH.sub.2 1 CH.sub.2                                                                               CHiPr    NH       CO                                    2.094                                                                              CH.sub.2 0         CHcPr    NH       CO                                    2.095                                                                              CH.sub.2 1 CH.sub.2                                                                               CHcPr    NH       CO                                    2.096                                                                              CH.sub.2 0         CHEt     NH       CO                                    2.098                                                                              CH.sub.2 0         CHEt     NMe      CO                                    2.099                                                                              CH.sub.2 0         CHEt     NCOMe    CO                                    2.100                                                                              CH.sub.2 0         CHEt     NCOEt    CO                                    2.101                                                                              CH.sub.2 0         CHEt     NCOnPr   CO                                    2.102                                                                              CH.sub.2 0         CHEt     NCOCH.sub.2 OMe                                                                         CO                                    2.103                                                                              CH.sub.2 0         CHEt     NCOCHMe.sub.2                                                                           CO                                    2.104                                                                              CH.sub.2 1 CH.sub.2                                                                               CHEt     NH       CO                                    2.106                                                                              CH.sub.2 1 CH.sub.2                                                                               CHEt     NMe      CO                                    2.107                                                                              CH.sub.2 1 CH.sub.2                                                                               CHEt     NCOMe    CO                                    2.108                                                                              CH.sub.2 1 CH.sub.2                                                                               CHEt     NCOEt    CO                                    2.109                                                                              CH.sub.2 1 CH.sub.2                                                                               CHEt     NCOnPr   CO                                    2.110                                                                              CH.sub.2 1 CH.sub.2                                                                               CHEt     NCOCH.sub.2 OMe                                                                         CO                                    2.111                                                                              CH.sub.2 1 CH.sub.2                                                                               CHEt     NCOCHMe.sub.2                                                                           CO                                    2.112                                                                              CH.sub.2 1 CMe     CH       NH       CO                                    2.113                                                                              CH.sub.2 1 CEt     CH       NH       CO                                    2.114                                                                              CH.sub.2 1 CH      CtBu     NMe      CO                                    2.115                                                                              CH       0         N        NCOCH.sub.3                                                                             CO                                    2.116                                                                              CH       0         N        NCONMe.sub.2                                                                            CNH                                   2.117                                                                              CH       0         N        NH       CO                                    2.118                                                                              CH       1 CH      NH       NH       CO                                    2.119                                                                              CH       1 CMe     CH.sub.2 NH       CO                                    2.120                                                                              CH       1 CEt     CH.sub.2 NH       CO                                    2.121                                                                              CH       0         CMe      NMe      CO                                    2.122                                                                              CH       1 CH      CHMe     NH       CO                                    2.123                                                                              CH       0         CtBu     NH       CO                                    2.124                                                                              CHMe     0         CH.sub.2 NH       CO                                    2.125                                                                              CHMe     0         CH.sub.2 NMe      CO                                    2.126                                                                              CHMe     0         CH.sub.2 NCOMe    CO                                    2.127                                                                              CHMe     0         CH.sub.2 NCOEt    CO                                    2.128                                                                              CHMe     0         CH.sub.2 NCOnPr   CO                                    2.129                                                                              CHMe     0         CH.sub.2 NCOCH.sub.2 OMe                                                                         CO                                    2.130                                                                              CHMe     0         CH.sub.2 NCOCHMe.sub.2                                                                           CO                                    2.131                                                                              CHMe     1 CH.sub.2                                                                               CH.sub.2 NH       CO                                    2.132                                                                              CHMe     1 CH.sub.2                                                                               CH.sub.2 NMe      CO                                    2.133                                                                              CHMe     1 CH.sub.2                                                                               CH.sub.2 NCOMe    CO                                    2.134                                                                              CHMe     1 CH.sub.2                                                                               CH.sub.2 NCOEt    CO                                    2.135                                                                              CHMe     1 CH.sub.2                                                                               CH.sub.2 NCOnPr   CO                                    2.136                                                                              CHMe     1 CH.sub.2                                                                               CH.sub.2 NCOCH.sub.2 OMe                                                                         CO                                    2.137                                                                              CHMe     1 CH.sub.2                                                                               CH.sub.2 NCOCHMe.sub.2                                                                           CO                                    2.138                                                                              CMe      0         C        NCH.sub.3                                                                               CO                                    2.139                                                                              CHMe     1 CH      CH       NH       CO                                    2.140                                                                              CHMe     0         CHMe     NH       CO                                    2.141                                                                              CHMe     0         CHMe     NMe      CO                                    2.142                                                                              CHMe     0         CHMe     NCOMe    CO                                    2.143                                                                              CHMe     0         CHMe     NCOEt    CO                                    2.144                                                                              CHMe     0         CHMe     NCOnPr   CO                                    2.145                                                                              CHMe     0         CHMe     NCOCH.sub.2 OMe                                                                         CO                                    2.146                                                                              CHMe     0         CHMe     NCOCHMe.sub.2                                                                           CO                                    2.147                                                                              CHMe     1 CH.sub.2                                                                               CHMe     NH       CO                                    2.148                                                                              CHMe     1 CH.sub.2                                                                               CHMe     NMe      CO                                    2.149                                                                              CHMe     1 CH.sub.2                                                                               CHMe     NCOMe    CO                                    2.150                                                                              CHMe     1 CH.sub.2                                                                               CHMe     NCOEt    CO                                    2.151                                                                              CHMe     1 CH.sub.2                                                                               CHMe     NCOnPr   CO                                    2.152                                                                              CHMe     1 CH.sub.2                                                                               CHMe     NCOCH.sub.2 OMe                                                                         CO                                    2.153                                                                              CHMe     1 CH.sub.2                                                                               CHMe     NCOCHMe.sub.2                                                                           CO                                    2.154                                                                              CHMe     0         CHEt     NH       CO                                    2.155                                                                              CHMe     0         CHEt     NMe      CO                                    2.156                                                                              CHMe     0         CHEt     NCOMe    CO                                    2.157                                                                              CHMe     0         CHEt     NCOEt    CO                                    2.158                                                                              CHMe     0         CHEt     NCOnPr   CO                                    2.159                                                                              CHMe     0         CHEt     NCOCH.sub.2 OMe                                                                         CO                                    2.160                                                                              CHMe     0         CHEt     NCOCHMe.sub.2                                                                           CO                                    2.161                                                                              CHMe     1 CH.sub.2                                                                               CHEt     NH       CO                                    2.162                                                                              CHMe     1 CH.sub.2                                                                               CHEt     NMe      CO                                    2.163                                                                              CHMe     1 CH.sub.2                                                                               CHEt     NCOMe    CO                                    2.164                                                                              CHMe     1 CH.sub.2                                                                               CHEt     NCOEt    CO                                    2.165                                                                              CHMe     1 CH.sub.2                                                                               CHEt     NCOnPr   CO                                    2.166                                                                              CHMe     1 CH.sub.2                                                                               CHEt     NCOCH.sub.2 OMe                                                                         CO                                    2.167                                                                              CHMe     1 CH.sub.2                                                                               CHEt     NCOCHMe.sub.2                                                                           CO                                    2.168                                                                              CHCH.sub.2 OMe                                                                          0         CH.sub.2 NH       CO                                    2.169                                                                              CHCH.sub.2 OMe                                                                          1 CH.sub.2                                                                               CH.sub.2 NH       CO                                    2.170                                                                              CHtBu    0         CH.sub.2 NH       CO                                    2.171                                                                              CHtBu    1 CH.sub.2                                                                               CH.sub.2 NH       CO                                    2.172                                                                              CHiPr    0         CH.sub.2 NH       CO                                    2.173                                                                              CHiPr    1 CH.sub.2                                                                               CH.sub.2 NH       CO                                    2.174                                                                              CHiPr    0         CH.sub.2 NH       CO                                    2.175                                                                              CHiPr    0         CH.sub.2 NMe      CO                                    2.176                                                                              CHiPr    0         CH.sub.2 NCOMe    CO                                    2.177                                                                              CHiPr    0         CH.sub.2 NCOEt    CO                                    2.178                                                                              CHiPr    0         CH.sub.2 NCOnPr   CO                                    2.179                                                                              CHiPr    0         CH.sub.2 NCOCH.sub.2 OMe                                                                         CO                                    2.180                                                                              CHiPr    0         CH.sub.2 NCOCHMe.sub.2                                                                           CO                                    2.181                                                                              CHiPr    1 CH.sub.2                                                                               CH.sub.2 NH       CO                                    2.182                                                                              CHiPr    1 CH.sub.2                                                                               CH.sub.2 NMe      CO                                    2.183                                                                              CHiPr    1 CH.sub.2                                                                               CH.sub.2 NCOMe    CO                                    2.184                                                                              CHiPr    1 CH.sub.2                                                                               CH.sub.2 NCOEt    CO                                    2.185                                                                              CHiPr    1 CH.sub.2                                                                               CH.sub.2 NCOnPr   CO                                    2.186                                                                              CHiPr    1 CH.sub.2                                                                               CH.sub.2 NCOCH.sub.2 OMe                                                                         CO                                    2.187                                                                              CHiPr    1 CH.sub.2                                                                               CH.sub.2 NCOCHMe.sub.2                                                                           CO                                    2.188                                                                              CHiPr    0         CHMe     NH       CO                                    2.189                                                                              CHiPr    0         CHMe     NMe      CO                                    2.190                                                                              CHiPr    0         CHMe     NCOMe    CO                                    2.191                                                                              CHiPr    0         CHMe     NCOEt    CO                                    2.192                                                                              CHiPr    0         CHMe     NCOnPr   CO                                    2.193                                                                              CHiPr    0         CHMe     NCOCH.sub.2 OMe                                                                         CO                                    2.194                                                                              CHiPr    0         CHMe     NCOCHMe.sub.2                                                                           CO                                    2.195                                                                              CHiPr    1 CH.sub.2                                                                               CHMe     NH       CO                                    2.196                                                                              CHiPr    1 CH.sub.2                                                                               CHMe     NMe      CO                                    2.197                                                                              CHiPr    1 CH.sub.2                                                                               CHMe     NCOMe    CO                                    2.198                                                                              CHiPr    1 CH.sub.2                                                                               CHMe     NCOEt    CO                                    2.199                                                                              CHiPr    1 CH.sub.2                                                                               CHMe     NCOnPr   CO                                    2.200                                                                              CHiPr    1 CH.sub.2                                                                               CHMe     NCOCH.sub.2 OMe                                                                         CO                                    2.201                                                                              CHiPr    1 CH.sub.2                                                                               CHMe     NCOCHMe.sub.2                                                                           CO                                    2.202                                                                              CHiPr    0         CHEt     NH       CO                                    2.203                                                                              CHiPr    0         CHEt     NMe      CO                                    2.204                                                                              CHiPr    0         CHEt     NCOMe    CO                                    2.205                                                                              CHiPr    0         CHEt     NCOEt    CO                                    2.206                                                                              CHiPr    0         CHEt     NCOnPr   CO                                    2.207                                                                              CHiPr    0         CHEt     NCOCH.sub.2 OMe                                                                         CO                                    2.208                                                                              CHiPr    0         CHEt     NCOCHMe.sub.2                                                                           CO                                    2.209                                                                              CHiPr    1 CH.sub.2                                                                               CHEt     NH       CO                                    2.210                                                                              CHiPr    1 CH.sub.2                                                                               CHEt     NMe      CO                                    2.211                                                                              CHiPr    1 CH.sub.2                                                                               CHEt     NCOMe    CO                                    2.212                                                                              CHiPr    1 CH.sub.2                                                                               CHEt     NCOEt    CO                                    2.213                                                                              CHiPr    1 CH.sub.2                                                                               CHEt     NCOnPr   CO                                    2.214                                                                              CHiPr    1 CH.sub.2                                                                               CHEt     NCOCH.sub.2 OMe                                                                         CO                                    2.215                                                                              CHiPr    1 CH.sub.2                                                                               CHEt     NCOCHMe.sub.2                                                                           CO                                    2.216                                                                              CHcPr    0         CH.sub.2 NH       CO                                    2.217                                                                              CHcPr    1 CH.sub.2                                                                               CH.sub.2 NH       CO                                    2.218                                                                              CHEt     0         CH.sub.2 NH       CO                                    2.219                                                                              CHEt     1 CH.sub.2                                                                               CH.sub.2 NH       CO                                    2.220                                                                              CHEt     0         CH.sub.2 NH       CO                                    2.221                                                                              CHEt     0         CH.sub.2 NMe      CO                                    2.222                                                                              CHEt     0         CH.sub.2 NCOMe    CO                                    2.223                                                                              CHEt     0         CH.sub.2 NCOEt    CO                                    2.224                                                                              CHEt     0         CH.sub.2 NCOnPr   CO                                    2.225                                                                              CHEt     0         CH.sub.2 NCOCH.sub.2 OMe                                                                         CO                                    2.226                                                                              CHEt     0         CH.sub.2 NCOCHMe.sub.2                                                                           CO                                    2.227                                                                              CHEt     1 CH.sub.2                                                                               CH.sub.2 NH       CO                                    2.228                                                                              CHEt     1 CH.sub.2                                                                               CH.sub.2 NMe      CO                                    2.229                                                                              CHEt     1 CH.sub.2                                                                               CH.sub.2 NCOMe    CO                                    2.230                                                                              CHEt     1 CH.sub.2                                                                               CH.sub.2 NCOEt    CO                                    2.231                                                                              CHEt     1 CH.sub.2                                                                               CH.sub.2 NCOnPr   CO                                    2.232                                                                              CHEt     1 CH.sub.2                                                                               CH.sub.2 NCOCH.sub.2 OMe                                                                         CO                                    2.233                                                                              CHEt     1 CH.sub.2                                                                               CH.sub.2 NCOCHMe.sub.2                                                                           CO                                    2.234                                                                              CHEt     0         CHMe     NH       CO                                    2.235                                                                              CHEt     0         CHMe     NMe      CO                                    2.236                                                                              CHEt     0         CHMe     NCOMe    CO                                    2.237                                                                              CHEt     0         CHMe     NCOEt    CO                                    2.238                                                                              CHEt     0         CHMe     NCOnPr   CO                                    2.239                                                                              CHEt     0         CHMe     NCOCH.sub.2 OMe                                                                         CO                                    2.240                                                                              CHEt     0         CHMe     NCOCHMe.sub.2                                                                           CO                                    2.241                                                                              CHEt     1 CH.sub.2                                                                               CHMe     NH       CO                                    2.242                                                                              CHEt     1 CH.sub.2                                                                               CHMe     NMe      CO                                    2.243                                                                              CHEt     1 CH.sub.2                                                                               CHMe     NCOMe    CO                                    2.244                                                                              CHEt     1 CH.sub.2                                                                               CHMe     NCOEt    CO                                    2.245                                                                              CHEt     1 CH.sub.2                                                                               CHMe     NCOnPr   CO                                    2.246                                                                              CHEt     1 CH.sub.2                                                                               CHMe     NCOCH.sub.2 OMe                                                                         CO                                    2.247                                                                              CHEt     1 CH.sub.2                                                                               CHMe     NCOCHMe.sub.2                                                                           CO                                    2.248                                                                              CHEt     0         CHEt     NH       CO                                    2.249                                                                              CHEt     0         CHEt     NMe      CO                                    2.250                                                                              CHEt     0         CHEt     NCOMe    CO                                    2.251                                                                              CHEt     0         CHEt     NCOEt    CO                                    2.252                                                                              CHEt     0         CHEt     NCOnPr   CO                                    2.253                                                                              CHEt     0         CHEt     NCOCH.sub.2 OMe                                                                         CO                                    2.254                                                                              CHEt     0         CHEt     NCOCHMe.sub.2                                                                           CO                                    2.255                                                                              CHEt     1 CH.sub.2                                                                               CHEt     NH       CO                                    2.256                                                                              CHEt     1 CH.sub.2                                                                               CHEt     NMe      CO                                    2.257                                                                              CHEt     1 CH.sub.2                                                                               CHEt     NCOMe    CO                                    2.258                                                                              CHEt     1 CH.sub.2                                                                               CHEt     NCOEt    CO                                    2.259                                                                              CHEt     1 CH.sub.2                                                                               CHEt     NCOnPr   CO                                    2.260                                                                              CHEt     1 CH.sub.2                                                                               CHEt     NCOCH.sub.2 OMe                                                                         CO                                    2.261                                                                              CHEt     1 CH.sub.2                                                                               CHEt     NCOCHMe.sub.2                                                                           CO                                    2.262                                                                              CSMe     1 N       CO       NMe      CO                                    2.263                                                                              CNHCOOEt 0         N        NH       CS                                    2.264                                                                              CNHCOOMe 0         N        NH       CS                                    2.265                                                                              CNHMe    1 N       CO       NMe      CO                                    2.266                                                                              CMe.sub.2                                                                               0         CO       NH       CO                                    2.267                                                                              CMe.sub.2                                                                               1 CH.sub.2                                                                               CO       NH       CO                                    2.268                                                                              CMe.sub.2                                                                               0         CH.sub.2 NH       CO                                    2.269                                                                              CMe.sub.2                                                                               1 CH.sub.2                                                                               CH.sub.2 NH       CO                                    2.270                                                                              CMe      0         CCOOEt   S        CNH                                   2.271                                                                              CMe      0         N        NH       CS                                    2.272                                                                              CMe      0         N        NH       CO                                    2.274                                                                              CMe      1 CH      NH       NH       CO                                    2.275                                                                              CMe      0         CH       S        CNH                                   2.276                                                                              CHMe     0         CH.sub.2 NH       CO                                    2.277                                                                              CMe      1 CH      CH.sub.2 NH       CO                                    2.278                                                                              CCH.sub.2 OMe                                                                           0         N        NH       CS                                    2.279                                                                              CCH.sub.2 OEt                                                                           0         N        NH       CS                                    2.280                                                                              CCH.sub.2 iPr                                                                           0         N        NH       CS                                    2.281                                                                              CCF.sub.3                                                                               0         N        NH       CS                                    2.282                                                                              CcHex    0         N        NH       CS                                    2.283                                                                              CiPr     0         N        NH       CS                                    2.284                                                                              CcPr     0         N        NH       CS                                    2.285                                                                              CEt      0         N        NH       CS                                    2.286                                                                              CEt      0         N        NH       CO                                    2.287                                                                              CC.sub.2 F.sub.5                                                                        0         N        NH       CS                                    2.288                                                                              CBr      0         N        NH       CS                                    2.289                                                                              C(NH)    0         CMe.sub.2                                                                               NH       CO                                    2.290                                                                              C(NH)    1 CH      CMe      NH       CO                                    2.291                                                                              CH.sub.2 1 CHMe    NH       NH       CO                                    2.292                                                                              CH.sub.2 1 CHEt    NH       NH       CO                                    2.293                                                                              CH.sub.2 1 CHcPr   NH       NH       CO                                    2.294                                                                              CH.sub.2 1 CHtBu   NH       NH       CO                                    2.295                                                                              CH.sub.2 1 CHCH.sub.2 OMe                                                                         NH       NH       CO                                    2.296                                                                              CHMe     1 CHMe    NH       NH       CO                                    2.297                                                                              CHMe     1 CHEt    NH       NH       CO                                    2.298                                                                              CHMe     1 CHcPr   NH       NH       CO                                    2.299                                                                              CHMe     1 CHtBu   NH       NH       CO                                    2.300                                                                              CHMe     1 CHCH.sub.2 OMe                                                                         NH       NH       CO                                    2.301                                                                              CMe.sub.2                                                                               1 CHMe    NH       NH       CO                                    2.302                                                                              CMe.sub.2                                                                               1 CHEt    NH       NH       CO                                    2.303                                                                              CMe.sub.2                                                                               1 CHcPr   NH       NH       CO                                    2.304                                                                              CMe.sub.2                                                                               1 CHtBu   NH       NH       CO                                    2.305                                                                              CMe.sub.2                                                                               1 CHCH.sub.2 OMe                                                                         NH       NH       CO                                    2.306                                                                              CH.sub.2 1 CHMe    NCOMe    NCOMe    CO                                    2.307                                                                              CH.sub.2 1 CHMe    NCOCH.sub.2 OMe                                                                         NCOCH.sub.2 OMe                                                                         CO                                    2.308                                                                              CH.sub.2 1 CHMe    NCOcPr   NCOcPr   CO                                    2.309                                                                              CH.sub.2 1 CHMe    NCOCH.sub.2 C1                                                                          NCOCH.sub.2 C1                                                                          CO                                    2.310                                                                              CH.sub.2 1 CHMe    NCOEt    NCOEt    CO                                    2.311                                                                              CH.sub.2 1 CHMe    NCOCHMe.sub.2                                                                           NCOCHMe.sub.2                                                                           CO                                    2.312                                                                              CH.sub.2 1 CHMe    NCOOEt   NCOOEt   CO                                    2.313                                                                              CH.sub.2 1 CHMe    NCOMe    NH       CO                                    2.314                                                                              CH.sub.2 1 CHMe    NCOCH.sub.2 OMe                                                                         NH       CO                                    2.315                                                                              CH.sub.2 1 CHMe    NCO-cPr  NH       CO                                    2.316                                                                              CH.sub.2 1 CHMe    NCOCH.sub.2 C1                                                                          NH       CO                                    2.317                                                                              CH.sub.2 1 CHMe    NCOEt    NH       CO                                    2.318                                                                              CH.sub.2 1 CHMe    NCOCHMe.sub.2                                                                           NH       CO                                    2.319                                                                              CH.sub.2 1 CHMe    NCOOEt   NH       CO                                    2.320                                                                              CH       0         C(Me)    N(NCH-3- CO                                                                    pyridinyl)                                     2.321                                                                              CH.sub.2 0         C(Me)(OH)                                                                               N(NCH-3- CO                                                                    pyridinyl)                                     __________________________________________________________________________

                  TABLE 2a                                                         ______________________________________                                         (melting points of compounds from Table 2)                                     Comp.                m.p.(°)                                            ______________________________________                                         2.001                207                                                       2.003                solid                                                     2.004                137-139                                                   2.005                142-143                                                   2.006                160                                                       2.008                192-193                                                   2.009                154                                                       2.010                212-213                                                   2.013                >250                                                      2.019                153-154                                                   2.020                50-51                                                     2.021                123-124                                                   2.030                176                                                       2.032                115-116                                                   2.040                64-68                                                     2.072                solid                                                     2.074                162-164                                                   2.080                solid                                                     2.114                81                                                        2.115                164-166                                                   2.116                228                                                       2.117                186-188                                                   2.121                115-119                                                   2.122                solid                                                     2.123                196-200                                                   2.138                solid                                                     2.139                solid                                                     2.262                169                                                       2.263                220-222                                                   2.265                220-221                                                   2.271                solid                                                     2.272                225-230                                                   2.275                169                                                       2.276                solid                                                     2.277                solid                                                     2.278                105                                                       2.279                115                                                       2.280                60                                                        2.281                140                                                       2.282                105                                                       2.283                118                                                       2.284                181                                                       2.285                150                                                       2.286                solid                                                     2.287                142                                                       2.288                135                                                       2.289                >250                                                      2.290                190-193                                                   ______________________________________                                    

                  TABLE 3                                                          ______________________________________                                          ##STR21##                                                                     Comp.    A          m        B         alkyl                                   ______________________________________                                         3.01     CO         1        CH.sub.2  Me                                      3.02     CO         1        CH.sub.2  Et                                      3.03     CO         1        CMe.sub.2 Me                                      3.04     CO         1        CMe.sub.2 Et                                      3.05     CO         0                  Me                                      3.06     CO         0                  Et                                      3.07     CH.sub.2   1        CHOH      Me                                      3.08     CH.sub.2   1        O         Me                                      3.09     CH.sub.2   1        NMe       Me                                      3.10     CH.sub.2   1        CO        Me                                      3.11     CH.sub.2   1        CH.sub.2  Et                                      3.12     CH.sub.2   1        CH.sub.2  Me                                      3.13     CH.sub.2   1        CH.sub.2  nPr                                     3.14     CH.sub.2   1        CH.sub.2  Et                                      3.15     CH.sub.2   1        CH.sub.2  nBu                                     3.16     CH.sub.2   1        C(OMe).sub.2                                                                             Me                                      3.17     CH.sub.2   1        C(OEt).sub.2                                                                             Me                                      3.18     CH.sub.2   1        CMe.sub.2 Me                                      3.19     CH.sub.2   1        CMe.sub.2 Et                                      3.20     CH.sub.2   1        CMe.sub.2 nPr                                     3.21     CH.sub.2   1        CHMe      Me                                      3.22     CH.sub.2   1        C(CH.sub.2 OH).sub.2                                                                     Me                                      3.23     CH.sub.2   1        CHEt      Me                                      3.24     CH.sub.2   0                  Me                                      3.25     CH.sub.2   0                  Et                                      3.26     CH.sub.2   0                  nPr                                     3.27     CH.sub.2   1        CH.sub.2  Me                                      3.28     CH.sub.2   1        CH.sub.2  Et                                      3.29     CH         1        CMe       Me                                      3.30     CH         1        CEt       Me                                      3.31     CH.sub.2   0                  Me                                      3.32     CH.sub.2   0                  Et                                      3.33     CHMe       1        CH.sub.2  Me                                      3.34     CHMe       1        CH.sub.2  Et                                      3.35     CHMe       0                  Me                                      3.36     CHMe       0                  Et                                      3.37     CHCH.sub.2 OMe                                                                            0                  Me                                      3.38     CHCH.sub.2 OMe                                                                            1        CH.sub.2  Me                                      3.39     CHtBu      0                  Me                                      3.40     CHtBu      1        CH.sub.2  Me                                      3.41     CHiPr      1        CH.sub.2  Me                                      3.42     CHiPr      1        CH.sub.2  Et                                      3.43     CHiPr      0                  Me                                      3.44     CHiPr      0                  Et                                      3.45     CHcPr      0                  Me                                      3.46     CHcPr      1        CH.sub.2  Me                                      3.47     CHEt       1        CH.sub.2  Me                                      3.48     CHEt       1        CH.sub.2  Et                                      3.49     CHEt       0                  Me                                      3.50     CHEt       0                  Et                                      3.51     CMe.sub.2  1        CH.sub.2  Me                                      3.52     CMe.sub.2  1        CH.sub.2  Et                                      3.53     CH.sub.2   0                  nPr                                     3.54     CH.sub.2   0                  nBu                                     ______________________________________                                    

                                      TABLE 3a                                     __________________________________________________________________________      ##STR22##                                                                     No.                                                                               A       m B     D       E        G                                          __________________________________________________________________________     a.001                                                                             CS      0       NH      NH       CS                                         a.002                                                                             CS      0       NH      NH       CO                                         a.003                                                                             CO      1 CMe   N       NH       CS                                         a.004                                                                             CO      1 C(C.sub.2 H.sub.4 iPr)                                                               N       NH       CS                                         a.005                                                                             CO      1 C(CH.sub.2 iPr)                                                                      N       NH       CS                                         a.006                                                                             CO      1 CtBu  N       NH       CS                                         a.007                                                                             CO      1 CtBu  N       NH       CO                                         a.008                                                                             CO      1 CcPr  N       NH       CS                                         a.009                                                                             CO      1 CcHex N       NH       CS                                         a.010                                                                             CO      1 NCH.sub.2 cHex                                                                       CO      NH       CO                                         a.011                                                                             CO      1 CH.sub.2                                                                             CO      NH       CO                                         a.012                                                                             CO      1 CH.sub.2                                                                             CH.sub.2                                                                               NH       CO                                         a.013                                                                             CO      1 CH.sub.2                                                                             CMe.sub.2                                                                              NH       CO                                         a.014                                                                             CO      1 CH    CMe     NH       CO                                         a.015                                                                             CO      1 CH    N       NH       CS                                         a.016                                                                             CO      1 CH    CCF.sub.3                                                                              NH       CNH                                        a.017                                                                             CO      1 CMe.sub.2                                                                            CO      NH       CO                                         a.018                                                                             CO      1 CMe.sub.2                                                                            CH.sub.2                                                                               NH       CO                                         a.019                                                                             CO      1 CMe   N       NH       CO                                         a.020                                                                             CO      1 CtBu  N       NCH.sub.2 CH.sub.2 F                                                                    CS                                         a.021                                                                             CO      1 CEt   N       NH       CS                                         a.022                                                                             CO      0       CO      NH       CO                                         a.023                                                                             CO      0       NH      NH       CO                                         a.024                                                                             CO      0       CH.sub.2                                                                               S        CS                                         a.025                                                                             CO      0       CHCH.sub.2 COOMe                                                                       NH       CS                                         a.026                                                                             CO      0       CHC.sub.2 H.sub.4 COOMe                                                                NH       CS                                         a.027                                                                             CO      0       NH      NH       CO                                         a.028                                                                             CO      0       CMeCHCMe.sub.2                                                                         NH       CO                                         a.029                                                                             CO      0       CMeCH.sub.2 CMe.sub.2                                                                  NH       CO                                         a.030                                                                             CO      0       CH.sub.2                                                                               NH       CS                                         a.031                                                                             CO      0       CMe.sub.2                                                                              NH       CO                                         a.032                                                                             CH.sub.2                                                                               0       CO      NMe      CS                                         a.033                                                                             CH.sub.2                                                                               0       CO      NiPr     CS                                         a.034                                                                             CH.sub.2                                                                               0       CO      NEt      CS                                         a.035                                                                             CH.sub.2                                                                               0       CO      NH       CO                                         a.036                                                                             CH.sub.2                                                                               0       CO      NH       CS                                         a.037                                                                             CH.sub.2                                                                               1 CMe.sub.2                                                                            CO      NH       CO                                         a.038                                                                             CH.sub.2                                                                               0       CO      NH       CO                                         a.039                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CO      NH       CO                                         a.040                                                                             CH.sub.2                                                                               0       CH.sub.2                                                                               O        CO                                         a.041                                                                             CH.sub.2                                                                               0       CH.sub.2                                                                               NH       CO                                         a.042                                                                             CH.sub.2                                                                               0       CH.sub.2                                                                               NH       CS                                         a.043                                                                             CH.sub.2                                                                               0       CH.sub.2                                                                               CH.sub.2 CO                                         a.044                                                                             CH.sub.2                                                                               0       CH.sub.2                                                                               NH       CO                                         a.045                                                                             CH.sub.2                                                                               0       CH.sub.2                                                                               NH       CO                                         a.046                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CH.sub.2                                                                               NH       CO                                         a.047                                                                             CH.sub.2                                                                               1 CMe.sub.2                                                                            CH.sub.2                                                                               NH       CO                                         a.048                                                                             CH.sub.2                                                                               1 CMe.sub.2                                                                            CH.sub.2                                                                               NH       CO                                         a.049                                                                             CH.sub.2                                                                               1 C(OMe).sub.2                                                                         CH.sub.2                                                                               NH       CO                                         a.050                                                                             CH.sub.2                                                                               1 C(OEt).sub.2                                                                         CH.sub.2                                                                               NH       CO                                         a.051                                                                             CH.sub.2                                                                               1 C(CH.sub.2 OH).sub.2                                                                 CH.sub.2                                                                               NH       CO                                         a.052                                                                             CH.sub.2                                                                               1 CO    CH.sub.2                                                                               NH       CO                                         a.053                                                                             CH.sub.2                                                                               1 CHOH  CH.sub.2                                                                               NH       CO                                         a.054                                                                             CH.sub.2                                                                               1 O     CH.sub.2                                                                               NH       CO                                         a.055                                                                             CH.sub.2                                                                               1 NMe   CH.sub.2                                                                               NH       CO                                         a.056                                                                             CH.sub.2                                                                               0       CH.sub.2                                                                               NH       CO                                         a.057                                                                             CH.sub.2                                                                               0       CH.sub.2                                                                               NMe      CO                                         a.058                                                                             CH.sub.2                                                                               0       CH.sub.2                                                                               NCOMe    CO                                         a.059                                                                             CH.sub.2                                                                               0       CH.sub.2                                                                               NCOEt    CO                                         a.060                                                                             CH.sub.2                                                                               0       CH.sub.2                                                                               NCOnPr   CO                                         a.061                                                                             CH.sub.2                                                                               0       CH.sub.2                                                                               NCOCH.sub.2 OMe                                                                         CO                                         a.062                                                                             CH.sub.2                                                                               0       CH.sub.2                                                                               NCOCHMe.sub.2                                                                           CO                                         a.063                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CH.sub.2                                                                               NH       CO                                         a.064                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CH.sub.2                                                                               NH       CO                                         a.065                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CH.sub.2                                                                               NMe      CO                                         a.066                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CH.sub.2                                                                               NCOMe    CO                                         a.067                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CH.sub.2                                                                               NCOEt    CO                                         a.068                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CH.sub.2                                                                               NCOnPr   CO                                         a.069                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CH.sub.2                                                                               NCOCH.sub.2 OMe                                                                         CO                                         a.070                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CH.sub.2                                                                               NCOCHMe.sub.2                                                                           CO                                         a.071                                                                             CH.sub.2                                                                               1 CH    CH      NH       CO                                         a.072                                                                             CH.sub.2                                                                               0       CHMe    NH       CO                                         a.073                                                                             CH.sub.2                                                                               0       CHMe    NH       CO                                         a.074                                                                             CH.sub.2                                                                               0       CHMe    NMe      CO                                         a.075                                                                             CH.sub.2                                                                               0       CHMe    NCOMe    CO                                         a.076                                                                             CH.sub.2                                                                               0       CHMe    NCOEt    CO                                         a.077                                                                             CH.sub.2                                                                               0       CHMe    NCOnPr   CO                                         a.078                                                                             CH.sub.2                                                                               0       CHMe    NCOCH.sub.2 OMe                                                                         CO                                         a.079                                                                             CH.sub.2                                                                               0       CHMe    NCOCHMe.sub.2                                                                           CO                                         a.080                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CHMe    NH       CO                                         a.081                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CHMe    NH       CO                                         a.082                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CHMe    NMe      CO                                         a.083                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CHMe    NCOMe    CO                                         a.084                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CHMe    NCOEt    CO                                         a.085                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CHMe    NCOnPr   CO                                         a.086                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CHMe    NCOCH.sub.2 OMe                                                                         CO                                         a.087                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CHMe    NCOCHMe.sub.2                                                                           CO                                         a.088                                                                             CH.sub.2                                                                               0       CHCH.sub.2 OMe                                                                         NH       CO                                         a.089                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CHCH.sub.2 OMe                                                                         NH       CO                                         a.090                                                                             CH.sub.2                                                                               0       CHtBu   NH       CO                                         a.091                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CHtBu   NH       CO                                         a.092                                                                             CH.sub.2                                                                               0       CHiPr   NH       CO                                         a.093                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CHiPr   NH       CO                                         a.094                                                                             CH.sub.2                                                                               0       CHcPr   NH       CO                                         a.095                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CHcPr   NH       CO                                         a.096                                                                             CH.sub.2                                                                               0       CHEt    NH       CO                                         a.097                                                                             CH.sub.2                                                                               0       CHEt    NH       CO                                         a.098                                                                             CH.sub.2                                                                               0       CHEt    NMe      CO                                         a.099                                                                             CH.sub.2                                                                               0       CHEt    NCOMe    CO                                         a.100                                                                             CH.sub.2                                                                               0       CHEt    NCOEt    CO                                         a.101                                                                             CH.sub.2                                                                               0       CHEt    NCOnPr   CO                                         a.102                                                                             CH.sub.2                                                                               0       CHEt    NCOCH.sub.2 OMe                                                                         CO                                         a.103                                                                             CH.sub.2                                                                               0       CHEt    NCOCHMe.sub.2                                                                           CO                                         a.104                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CHEt    NH       CO                                         a.105                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CHEt    NH       CO                                         a.106                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CHEt    NMe      CO                                         a.107                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CHEt    NCOMe    CO                                         a.108                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CHEt    NCOEt    CO                                         a.109                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CHEt    NCOnPr   CO                                         a.110                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CHEt    NCOCH.sub.2 OMe                                                                         CO                                         a.111                                                                             CH.sub.2                                                                               1 CH.sub.2                                                                             CHEt    NCOCHMe.sub.2                                                                           CO                                         a.112                                                                             CH.sub.2                                                                               1 CMe   CH      NH       CO                                         a.113                                                                             CH.sub.2                                                                               1 CEt   CH      NH       CO                                         a.114                                                                             CH.sub.2                                                                               1 CH    CtBu    NMe      CO                                         a.115                                                                             CH      0       N       NCOCH.sub.3                                                                             CO                                         a.116                                                                             CH      0       N       NCONMe.sub.2                                                                            CNH                                        a.117                                                                             CH      0       N       NH       CO                                         a.118                                                                             CH      1 CH    NH      NH       CO                                         a.119                                                                             CH      1 CMe   CH.sub.2                                                                               NH       CO                                         a.120                                                                             CH      1 CEt   CH.sub.2                                                                               NH       CO                                         a.121                                                                             CH      0       CMe     NH       CO                                         a.122                                                                             CH      1 CH    CHMe    NH       CO                                         a.123                                                                             CH      0       CtBu    NH       CO                                         a.124                                                                             CHMe    0       CH.sub.2                                                                               NH       CO                                         a.125                                                                             CHMe    0       CH.sub.2                                                                               NMe      CO                                         a.126                                                                             CHMe    0       CH.sub.2                                                                               NCOMe    CO                                         a.127                                                                             CHMe    0       CH.sub.2                                                                               NCOEt    CO                                         a.128                                                                             CHMe    0       CH.sub.2.                                                                              NCOnPr   CO                                         a.129                                                                             CHMe    0       CH.sub.2                                                                               NCOCH.sub.2 OMe                                                                         CO                                         a.130                                                                             CHMe    0       CH.sub.2                                                                               NCOCHMe.sub.2                                                                           CO                                         a.131                                                                             CHMe    1 CH.sub.2                                                                             CH.sub.2                                                                               NH       CO                                         a.132                                                                             CHMe    1 CH.sub.2                                                                             CH.sub.2                                                                               NMe      CO                                         a.133                                                                             CHMe    1 CH.sub.2                                                                             CH.sub.2                                                                               NCOMe    CO                                         a.134                                                                             CHMe    1 CH.sub.2                                                                             CH.sub.2                                                                               NCOEt    CO                                         a.135                                                                             CHMe    1 CH.sub.2                                                                             CH.sub.2                                                                               NCOnPr   CO                                         a.136                                                                             CHMe    1 CH.sub.2                                                                             CH.sub.2                                                                               NCOCH.sub.2 OMe                                                                         CO                                         a.137                                                                             CHMe    1 CH.sub.2                                                                             CH.sub.2                                                                               NCOCHMe.sub.2                                                                           CO                                         a.138                                                                             CMe     0       CH      NCH.sub.3                                                                               CO                                         a.139                                                                             CHMe    1 CH    CH      NH       CO                                         a.140                                                                             CHMe    0       CHMe    NH       CO                                         a.141                                                                             CHMe    0       CHMe    NMe      CO                                         a.142                                                                             CHMe    0       CHMe    NCOMe    CO                                         a.143                                                                             CHMe    0       CHMe    NCOEt    CO                                         a.144                                                                             CHMe    0       CHMe    NCOnPr   CO                                         a.145                                                                             CHMe    0       CHMe    NCOCH.sub.2 OMe                                                                         CO                                         a.146                                                                             CHMe    0       CHMe    NCOCHMe.sub.2                                                                           CO                                         a.147                                                                             CHMe    1 CH.sub.2                                                                             CHMe    NH       CO                                         a.148                                                                             CHMe    1 CH.sub.2                                                                             CHMe    NMe      CO                                         a.149                                                                             CHMe    1 CH.sub.2                                                                             CHMe    NCOMe    CO                                         a.150                                                                             CHMe    1 CH.sub.2                                                                             CHMe    NCOEt    CO                                         a.151                                                                             CHMe    1 CH.sub.2                                                                             CHMe    NCOnPr   CO                                         a.152                                                                             CHMe    1 CH.sub.2                                                                             CHMe    NCOCH.sub.2 OMe                                                                         CO                                         a.153                                                                             CHMe    1 CH.sub.2                                                                             CHMe    NCOCHMe.sub.2                                                                           CO                                         a.154                                                                             CHMe    0       CHEt    NH       CO                                         a.155                                                                             CHMe    0       CHEt    NMe      CO                                         a.156                                                                             CHMe    0       CHEt    NCOMe    CO                                         a.157                                                                             CHMe    0       CHEt    NCOEt    CO                                         a.158                                                                             CHMe    0       CHEt    NCOnPr   CO                                         a.159                                                                             CHMe    0       CHEt    NCOCH.sub.2 OMe                                                                         CO                                         a.160                                                                             CHMe    0       CHEt    NCOCHMe.sub.2                                                                           CO                                         a.161                                                                             CHMe    1 CH.sub.2                                                                             CHEt    NH       CO                                         a.162                                                                             CHMe    1 CH.sub.2                                                                             CHEt    NMe      CO                                         a.163                                                                             CHMe    1 CH.sub.2                                                                             CHEt    NCOMe    CO                                         a.164                                                                             CHMe    1 CH.sub.2                                                                             CHEt    NCOEt    CO                                         a.165                                                                             CHMe    1 CH.sub.2                                                                             CHEt    NCOnPr   CO                                         a.166                                                                             CHMe    1 CH.sub.2                                                                             CHEt    NCOCH.sub.2 OMe                                                                         CO                                         a.167                                                                             CHMe    1 CH.sub.2                                                                             CHEt    NCOCHMe.sub.2                                                                           CO                                         a.168                                                                             CHCH.sub.2 OMe                                                                         0       CH.sub.2                                                                               NH       CO                                         a.169                                                                             CHCH.sub.2 OMe                                                                         1 CH.sub.2                                                                             CH.sub.2                                                                               NH       CO                                         a.170                                                                             CHtBu   0       CH.sub.2                                                                               NH       CO                                         a.171                                                                             CHtBu   1 CH.sub.2                                                                             CH.sub.2                                                                               NH       CO                                         a.172                                                                             CHiPr   0       CH.sub.2                                                                               NH       CO                                         a.173                                                                             CHiPr   1 CH.sub.2                                                                             CH.sub.2                                                                               NH       CO                                         a.174                                                                             CHiPr   0       CH.sub.2                                                                               NH       CO                                         a.175                                                                             CHiPr   0       CH.sub.2                                                                               NMe      CO                                         a.176                                                                             CHiPr   0       CH.sub.2                                                                               NCOMe    CO                                         a.177                                                                             CHiPr   0       CH.sub.2                                                                               NCOEt    CO                                         a.178                                                                             CHiPr   0       CH.sub.2                                                                               NCOnPr   CO                                         a.179                                                                             CHiPr   0       CH.sub.2                                                                               NCOCH.sub.2 OMe                                                                         CO                                         a.180                                                                             CHiPr   0       CH.sub.2                                                                               NCOCHMe.sub.2                                                                           CO                                         a.181                                                                             CHiPr   1 CH.sub.2                                                                             CH.sub.2                                                                               NH       CO                                         a.182                                                                             CHiPr   1 CH.sub.2                                                                             CH.sub.2                                                                               NMe      CO                                         a.183                                                                             CHiPr   1 CH.sub.2                                                                             CH.sub.2                                                                               NCOMe    CO                                         a.184                                                                             CHiPr   1 CH.sub.2                                                                             CH.sub.2                                                                               NCOEt    CO                                         a.185                                                                             CHiPr   1 CH.sub.2                                                                             CH.sub.2                                                                               NCOnPr   CO                                         a.186                                                                             CHiPr   I CH.sub.2                                                                             CH.sub.2                                                                               NCOCH.sub.2 OMe                                                                         CO                                         a.187                                                                             CHiPr   1 CH.sub.2                                                                             CH.sub.2                                                                               NCOCHMe.sub.2                                                                           CO                                         a.188                                                                             CHiPr   0       CHMe    NH       CO                                         a.189                                                                             CHiPr   0       CHMe    NMe      CO                                         a.190                                                                             CHiPr   0       CHMe    NCOMe    CO                                         a.191                                                                             CHiPr   0       CHMe    NCOEt    CO                                         a.192                                                                             CHiPr   0       CHMe    NCOnPr   CO                                         a.193                                                                             CHiPr   0       CHMe    NCOCH.sub.2 OMe                                                                         CO                                         a.194                                                                             CHiPr   0       CHMe    NCOCHMe.sub.2                                                                           CO                                         a.195                                                                             CHiPr   1 CH.sub.2                                                                             CHMe    NH       CO                                         a.196                                                                             CHiPr   1 CH.sub.2                                                                             CHMe    NMe      CO                                         a.197                                                                             CHiPr   1 CH.sub.2                                                                             CHMe    NCOMe    CO                                         a.198                                                                             CHiPr   1 CH.sub.2                                                                             CHMe    NCOEt    CO                                         a.199                                                                             CHiPr   1 CH.sub.2                                                                             CHMe    NCOnPr   CO                                         a.200                                                                             CHiPr   1 CH.sub.2                                                                             CHMe    NCOCH.sub.2 OMe                                                                         CO                                         a.201                                                                             CHiPr   1 CH.sub.2                                                                             CHMe    NCOCHMe.sub.2                                                                           CO                                         a.202                                                                             CHiPr   0       CHEt    NH       CO                                         a.203                                                                             CHiPr   0       CHEt    NMe      CO                                         a.204                                                                             CHiPr   0       CHEt    NCOMe    CO                                         a.205                                                                             CHiPr   0       CHEt    NCOEt    CO                                         a.206                                                                             CHiPr   0       CHEt    NCOnPr   CO                                         a.207                                                                             CHiPr   0       CHEt    NCOCH.sub.2 OMe                                                                         CO                                         a.208                                                                             CHiPr   0       CHEt    NCOCHMe.sub.2                                                                           CO                                         a.209                                                                             CHiPr   1 CH.sub.2                                                                             CHEt    NH       CO                                         a.210                                                                             CHiPr   1 CH.sub.2                                                                             CHEt    NMe      CO                                         a.211                                                                             CHiPr   1 CH.sub.2                                                                             CHEt    NCOMe    CO                                         a.212                                                                             CHiPr   1 CH.sub.2                                                                             CHEt    NCOEt    CO                                         a.213                                                                             CHiPr   1 CH.sub.2                                                                             CHEt    NCOnPr   CO                                         a.214                                                                             CHiPr   1 CH.sub.2                                                                             CHEt    NCOCH.sub.2 OMe                                                                         CO                                         a.215                                                                             CHiPr   1 CH.sub.2                                                                             CHEt    NCOCHMe.sub.2                                                                           CO                                         a.216                                                                             CHcPr   0       CH.sub.2                                                                               NH       CO                                         a.217                                                                             CHcPr   1 CH.sub.2                                                                             CH.sub.2                                                                               NH       CO                                         a.218                                                                             CHEt    0       CH.sub.2                                                                               NH       CO                                         a.219                                                                             CHEt    1 CH.sub.2                                                                             CH.sub.2                                                                               NH       CO                                         a.220                                                                             CHEt    0       CH.sub.2                                                                               NH       CO                                         a.221                                                                             CHEt    0       CH.sub.2                                                                               NMe      CO                                         a.222                                                                             CHEt    0       CH.sub.2                                                                               NCOMe    CO                                         a.223                                                                             CHEt    0       CH.sub.2                                                                               NCOEt    CO                                         a.224                                                                             CHEt    0       CH.sub.2                                                                               NCOnPr   CO                                         a.225                                                                             CHEt    0       CH.sub.2                                                                               NCOCH.sub.2 OMe                                                                         CO                                         a.226                                                                             CHEt    0       CH.sub.2                                                                               NCOCHMe.sub.2                                                                           CO                                         a.227                                                                             CHEt    1 CH.sub.2                                                                             CH.sub.2                                                                               NH       CO                                         a.228                                                                             CHEt    1 CH.sub.2                                                                             CH.sub.2                                                                               NMe      CO                                         a.229                                                                             CHEt    1 CH.sub.2                                                                             CH.sub.2                                                                               NCOMe    CO                                         a.230                                                                             CHEt    1 CH.sub.2                                                                             CH.sub.2                                                                               NCOEt    CO                                         a.231                                                                             CHEt    1 CH.sub.2                                                                             CH.sub.2                                                                               NCOnPr   CO                                         a.232                                                                             CHEt    1 CH.sub.2                                                                             CH.sub.2                                                                               NCOCH.sub.2 OMe                                                                         CO                                         a.233                                                                             CHEt    1 CH.sub.2                                                                             CH.sub.2                                                                               NCOCHMe.sub.2                                                                           CO                                         a.234                                                                             CHEt    0       CHMe    NH       CO                                         a.235                                                                             CHEt    0       CHMe    NMe      CO                                         a.236                                                                             CHEt    0       CHMe    NCOMe    CO                                         a.237                                                                             CHEt    0       CHMe    NCOEt    CO                                         a.238                                                                             CHEt    0       CHMe    NCOnPr   CO                                         a.239                                                                             CHEt    0       CHMe    NCOCH.sub.2 OMe                                                                         CO                                         a.240                                                                             CHEt    0       CHMe    NCOCHMe.sub.2                                                                           CO                                         a.241                                                                             CHEt    1 CH.sub.2                                                                             CHMe    NH       CO                                         a.242                                                                             CHEt    1 CH.sub.2                                                                             CHMe    NMe      CO                                         a.243                                                                             CHEt    1 CH.sub.2                                                                             CHMe    NCOMe    CO                                         a.244                                                                             CHEt    1 CH.sub.2                                                                             CHMe    NCOEt    CO                                         a.245                                                                             CHEt    1 CH.sub.2                                                                             CHMe    NCOnPr   CO                                         a.246                                                                             CHEt    1 CH.sub.2                                                                             CHMe    NCOCH.sub.2 OMe                                                                         CO                                         a.247                                                                             CHEt    1 CH.sub.2                                                                             CHMe    NCOCHMe.sub.2                                                                           CO                                         a.248                                                                             CHEt    0       CHEt    NH       CO                                         a.249                                                                             CHEt    0       CHEt    NMe      CO                                         a.250                                                                             CHEt    0       CHEt    NCOMe    CO                                         a.251                                                                             CHEt    0       CHEt    NCOEt    CO                                         a.252                                                                             CHEt    0       CHEt    NCOnPr   CO                                         a.253                                                                             CHEt    0       CHEt    NCOCH.sub.2 OMe                                                                         CO                                         a.254                                                                             CHEt    0       CHEt    NCOCHMe.sub.2                                                                           CO                                         a.255                                                                             CHEt    1 CH.sub.2                                                                             CHEt    NH       CO                                         a.256                                                                             CHEt    1 CH.sub.2                                                                             CHEt    NMe      CO                                         a.257                                                                             CHEt    1 CH.sub.2                                                                             CHEt    NCOMe    CO                                         a.258                                                                             CHEt    1 CH.sub.2                                                                             CHEt    NCOEt    CO                                         a.259                                                                             CHEt    1 CH.sub.2                                                                             CHEt    NCOnPr   CO                                         a.260                                                                             CHEt    1 CH.sub.2                                                                             CHEt    NCOCH.sub.2 OMe                                                                         CO                                         a.261                                                                             CHEt    1 CH.sub.2                                                                             CHEt    NCOCHMe.sub.2                                                                           CO                                         a.262                                                                             C(SMe)  1 N     CO      NMe      CO                                         a.263                                                                             C(NHCOOEt)                                                                             0       N       NH       CS                                         a.264                                                                             C(NHCOOMe)                                                                             0       N       NH       CS                                         a.265                                                                             C(NHMe) 1 N     CO      NMe      CO                                         a.266                                                                             CMe     0       CO      NH       CO                                         a.267                                                                             CMe     1 CH.sub.2                                                                             CO      NH       CO                                         a.268                                                                             CMe     0       CH.sub.2                                                                               NH       CO                                         a.269                                                                             CMe     1 CH.sub.2                                                                             CH.sub.2                                                                               NH       CO                                         a.270                                                                             CMe     0       C(COOEt)                                                                               S        CNH                                        a.271                                                                             CMe     0       N       NH       CS                                         a.272                                                                             CMe     0       N       NH       CO                                         a.273                                                                             CMe     0       CH      NH       CO                                         a.274                                                                             CMe     1 CH    NH      NH       CO                                         a.275                                                                             CMe     0       CH      S        CNH                                        a.276                                                                             CHMe    0       CH.sub.2                                                                               NH       CO                                         a.277                                                                             CMe     1 CH    CH2     NH       CO                                         a.278                                                                             C(CH.sub.2 OMe)                                                                        0       N       NH       CS                                         a.279                                                                             C(CH.sub.2 OEt)                                                                        0       N       NH       CS                                         a.280                                                                             C(CH.sub.2 iPr)                                                                        0       N       NH       CS                                         a.281                                                                             CCF.sub.3                                                                              0       N       NH       CS                                         a.282                                                                             C(C.sub.5 H.sub.11)                                                                    0       N       NH       CS                                         a.283                                                                             CiPr    0       N       NH       CS                                         a.284                                                                             CcPr    0       N       NH       CS                                         a.285                                                                             CEt     0       N       NH       CS                                         a.286                                                                             CEt     0       N       NH       CO                                         a.287                                                                             C(C.sub.2 F.sub.5)                                                                     0       N       NH       CS                                         a.288                                                                             CBr     0       N       NH       CS                                         a.289                                                                             C(NH)   0       CMe.sub.2                                                                              NH       CO                                         a.290                                                                             C(NH)   1 CH    CMe     NH       CO                                         a.291                                                                             CH.sub.2                                                                               1 CHMe  NH      NH       CO                                         a.292                                                                             CH.sub.2                                                                               1 CHEt  NH      NH       CO                                         a.293                                                                             CH.sub.2                                                                               1 CHcPr NH      NH       CO                                         a.294                                                                             CH.sub.2                                                                               1 CHtBu NH      NH       CO                                         a.295                                                                             CH.sub.2                                                                               1 CHCH.sub.2 OMe                                                                       NH      NH       CO                                         a.296                                                                             CHMe    1 CHMe  NH      NH       CO                                         a.297                                                                             CHMe    1 CHEt  NH      NH       CO                                         a.298                                                                             CHMe    1 CHcPr NH      NH       CO                                         a.299                                                                             CHMe    1 CHtBu NH      NH       CO                                         a.300                                                                             CHMe    1 CHCH.sub.2 OMe                                                                       NH      NH       CO                                         a.301                                                                             CMe.sub.2                                                                              1 CHMe  NH      NH       CO                                         a.302                                                                             CMe.sub.2                                                                              1 CHEt  NH      NH       CO                                         a.303                                                                             CMe.sub.2                                                                              1 CHcPr NH      NH       CO                                         a.304                                                                             CMe.sub.2                                                                              1 CHtBu NH      NH       CO                                         a.305                                                                             CMe.sub.2                                                                              1 CHCH.sub.2 OMe                                                                       NH      NH       CO                                         a.306                                                                             CH.sub.2                                                                               1 CHMe  NCOMe   NCOMe    CO                                         a.307                                                                             CH.sub.2                                                                               1 CHMe  NCOCH.sub.2 OMe                                                                        NCOCH.sub.2 OMe                                                                         CO                                         a.308                                                                             CH.sub.2                                                                               1 CHMe  NCOcPr  NCOcPr   CO                                         a.309                                                                             CH.sub.2                                                                               1 CHMe  NCOCH.sub.2 Cl                                                                         NCOCH.sub.2 Cl                                                                          CO                                         a.310                                                                             CH.sub.2                                                                               1 CHMe  NCOEt   NCOEt    CO                                         a.311                                                                             CH.sub.2                                                                               1 CHMe  NCOCHMe.sub.2                                                                          NCOCHMe.sub.2                                                                           CO                                         a.312                                                                             CH.sub.2                                                                               1 CHMe  NCOOEt  NCOOEt   CO                                         a.313                                                                             CH.sub.2                                                                               1 CHMe  NCOMe   NH       CO                                         a.314                                                                             CH.sub.2                                                                               1 CHMe  NCOCH.sub.2 OMe                                                                        NH       CO                                         a.315                                                                             CH.sub.2                                                                               1 CHMe  NCOcPr  NH       CO                                         a.316                                                                             CH.sub.2                                                                               1 CHMe  NCOCH.sub.2 Cl                                                                         NH       CO                                         a.317                                                                             CH.sub.2                                                                               1 CHMe  NCOEt   NH       CO                                         a.318                                                                             CH.sub.2                                                                               1 CHMe  NCOCHMe.sub.2                                                                          NH       CO                                         a.319                                                                             CH.sub.2                                                                               1 CHMe  NCOOEt  NH       CO                                         a.320                                                                             CH      0       CMe     N(NCH-3- CO                                                                    pyridyl)                                            a.321                                                                             CH2     0       C(Me)(OH)                                                                              N(NCH-3- CO                                                                    pyridyl)                                            a.322                                                                             CH      0       CMe     N(NCH2)  CO                                         a.323                                                                             CH2     0       C(Me)(OH)                                                                              N(NCH2)  CO                                         __________________________________________________________________________

                  TABLE 3b                                                         ______________________________________                                         (melting points of compounds from Table 3a)                                           Comp. m.p.(°)                                                    ______________________________________                                                3a.121                                                                               182-184                                                                  3a.273                                                                               189-196                                                           ______________________________________                                    

EXAMPLE P18 (4-Methyl-2-oxoimidazolidin-1-yl)acetamide (Compound 4.025 in Table 4)

1.6 g of Rh/C are added to a solution of 7.8 g of (4-methyl-2-oxo-1,3-dihydroimidazol-1-yl)acetamide in 80 ml of methanol and the reaction mixture is treated with hydrogen at 3 bar. After 30 minutes, 1.13 litres of hydrogen have been taken up and the reaction has ceased. The reaction mixture is then filtered over Celite and concentrated by evaporation. The residue is dissolved in methylene chloride, magnesium sulfate is added thereto, followed by filtration over Celite and concentration by evaporation. The residue is stirred with ether. The crystals are filtered off with suction and dried in vacuo at 60°. 7.3 g of the title compound having a melting point of 124°-127 are thus obtained.

EXAMPLE P19 (3,4-Dimethyl-2-oxo-1,3-dihydroimidazol-1-yl)acetamide (Compound 4.047 in Table 4)

68.5 ml of methylamine (40% in water) are added dropwise to a solution of 78 g of 5-methyl-2-oxo-3-(2-oxopropyl)-3H-1,3,4-oxadiazole in 500 ml of acetonitrile. After the slightly endothermic reaction, the orange-coloured solution is heated to 480°. After 30 minutes the reaction mixture is concentrated by evaporation. 100 ml of tetrahydrofuran and 200 ml of ethyl acetate are added to the residue, whereupon crystals precipitate. The crystals are filtered off, then washed with ethyl acetate and dried in vacuo at 60°. A mixture of title compound and (3,4-dimethyl-2-oxo-4-methylamino-1,3-dihydroimidazol-1-yl)acetamide is obtained. A sample of that mixture is separated on silica gel with ethyl acetate/methanol (2:1). The title compound having a melting point of 198°-201° and (3,4-dimethyl-2-oxo-4-methylamino-1,3-dihydroimidazol-1-yl)acetamide having a melting point of 150°-152° (decomposition) are obtained. A sample of the above-mentioned mixture is maintained at 175° until no further evolution of methylamine gas is observed. The cooled residue is stirred with a small amount of methanol. Filtration of the suspension likewise yields the title compound having a melting point of 199°-201°.

EXAMPLE P20

The other compounds listed in Tables 4 and 4a can also be prepared in a manner analogous to that described in Examples P18 and P19.

                  TABLE 4                                                          ______________________________________                                          ##STR23##                                                                     Comp. A         mB         D       E    G   alkyl                              ______________________________________                                         4.001.                                                                               CO        1CMe.sub.2 CO      NH   CO  Me                                 4.002.                                                                               CO        1CMe.sub.2 CH.sub.2                                                                               NH   CO  Me                                 4.003.                                                                               CO        0          CH.sub.2                                                                               NH   CO  Me                                 4.004.                                                                               CO        1CH.sub.2  CH.sub.2                                                                               NH   CO  Me                                 4.005.                                                                               CO        0          CMe.sub.2                                                                              NH   CO  Me                                 4.006.                                                                               CO        1CH.sub.2  CMe.sub.2                                                                              NH   CO  Me                                 4.007.                                                                               CH.sub.2  1CMe.sub.2 CO      NH   CO  Me                                 4.008.                                                                               CH.sub.2  0          CO      NH   CO  Me                                 4.009.                                                                               CH.sub.2  1CH.sub.2  CO      NH   CO  Me                                 4.010.                                                                               CH.sub.2  0          CH.sub.2                                                                               NH   CO  Me                                 4.011.                                                                               CH.sub.2  1CH.sub.2  CH.sub.2                                                                               NH   CO  Me                                 4.012.                                                                               CH.sub.2  1CMe.sub.2 CH.sub.2                                                                               NH   CO  Me                                 4.013.                                                                               CH.sub.2  1CMe.sub.2 CH.sub.2                                                                               NH   CO  Me                                 4.014.                                                                               CH.sub.2  1C(OMe).sub.2                                                                             CH.sub.2                                                                               NH   CO  Me                                 4.015.                                                                               CH.sub.2  1C(OEt).sub.2                                                                             CH.sub.2                                                                               NH   CO  Me                                 4.016.                                                                               CH.sub.2  1C(CH.sub.2 OH).sub.2                                                                     CH.sub.2                                                                               NH   CO  Me                                 4.017.                                                                               CH.sub.2  1CO        CH.sub.2                                                                               NH   CO  Me                                 4.018.                                                                               CH.sub.2  1CHOH      CH.sub.2                                                                               NH   CO  Me                                 4.019.                                                                               CH.sub.2  1O         CH.sub.2                                                                               NH   CO  Me                                 4.020.                                                                               CH.sub.2  1NMe       CH.sub.2                                                                               NH   CO  Me                                 4.021.                                                                               CH.sub.2  0          CH.sub.2                                                                               NH   CO  Me                                 4.022.                                                                               CH.sub.2  1CH.sub.2  CH.sub.2                                                                               NH   CO  Me                                 4.023.                                                                               CH.sub.2  1CH.sub.2  CH.sub.2                                                                               NH   CO  Me                                 4.024.                                                                               CH.sub.2  1CH        CH      NH   CO  Me                                 4.025.                                                                               CH.sub.2  0          CHMe    NH   CO  Me                                 4.026.                                                                               CH.sub.2  0          CHMe    NH   CO  Me                                 4.027.                                                                               CH.sub.2  1CH.sub.2  CHMe    NH   CO  Me                                 4.028.                                                                               CH.sub.2  1CH.sub.2  CHMe    NH   CO  Me                                 4.029.                                                                               CH.sub.2  0          CHCH.sub.2 OMe                                                                         NH   CO  Me                                 4.030.                                                                               CH.sub.2  1CH.sub.2  CHCH.sub.2 OMe                                                                         NH   CO  Me                                 4.031.                                                                               CH.sub.2  0          CHtBu   NH   CO  Me                                 4.032.                                                                               CH.sub.2  1CH.sub.2  CHtBu   NH   CO  Me                                 4.033.                                                                               CH.sub.2  0          CHiPr   NH   CO  Me                                 4.034.                                                                               CH.sub.2  1CH.sub.2  CHiPr   NH   CO  Me                                 4.035.                                                                               CH.sub.2  0          CHcPr   NH   CO  Me                                 4.036.                                                                               CH.sub.2  1CH.sub.2  CHcPr   NH   CO  Me                                 4.037.                                                                               CH.sub.2  0          CHEt    NH   CO  Me                                 4.038.                                                                               CH.sub.2  0          CHEt    NH   CO  Me                                 4.039.                                                                               CH.sub.2  1CH.sub.2  CHEt    NH   CO  Me                                 4.040.                                                                               CH.sub.2  1CH.sub.2  CHEt    NH   CO  Me                                 4.041.                                                                               CH.sub.2  1CMe       C       NH   CO  Me                                 4.042.                                                                               CH.sub.2  1CEt       C       NH   CO  Me                                 4.043.                                                                               CH        0          N       NH   CO  Me                                 4.044.                                                                               CH        1CH.sub.2  N       NH   CO  Me                                 4.045.                                                                               CH        1CMe       CH.sub.2                                                                               NH   CO  Me                                 4.046.                                                                               CH        1CEt       CH.sub.2                                                                               NH   CO  Me                                 4.047.                                                                               CH        0          CMe     NMe  CO  Me                                 4.048.                                                                               CH        1CH        CHMe    NH   CO  Me                                 4.049.                                                                               CMe       0          CH      NH   CO  Me                                 4.050.                                                                               CHMe      1CH        CH      NH   CO  Me                                 4.051.                                                                               CHMe      0          CH.sub.2                                                                               NH   CO  Me                                 4.052.                                                                               CHMe      1CH.sub.2  CH.sub.2                                                                               NH   CO  Me                                 4.053.                                                                               CHMe      0          CHMe    NH   CO  Me                                 4.054.                                                                               CHMe      1CH.sub.2  CHMe    NH   CO  Me                                 4.055.                                                                               CHMe      0          CHEt    NH   CO  Me                                 4.056.                                                                               CHMe      1CH.sub.2  CHEt    NH   CO  Me                                 4.057.                                                                               CHCH.sub.2 OMe                                                                           0          CH.sub.2                                                                               NH   CO  Me                                 4.058.                                                                               CHCH.sub.2 OMe                                                                           1CH.sub.2  CH.sub.2                                                                               NH   CO  Me                                 4.059.                                                                               CHtBu     0          CH.sub.2                                                                               NH   CO  Me                                 4.060.                                                                               CHtBu     1CH.sub.2  CH.sub.2                                                                               NH   CO  Me                                 4.061.                                                                               CHiPr     0          CH.sub.2                                                                               NH   CO  Me                                 4.062.                                                                               CHiPr     1CH.sub.2  CH.sub.2                                                                               NH   CO  Me                                 4.063.                                                                               CHiPr     0          CH.sub.2                                                                               NH   CO  Me                                 4.064.                                                                               CHiPr     1CH.sub.2  CH.sub.2                                                                               NH   CO  Me                                 4.065.                                                                               CHiPr     0          CHMe    NH   CO  Me                                 4.066.                                                                               CHiPr     1CH.sub.2  CHMe    NH   CO  Me                                 4.067.                                                                               CHiPr     0          CHEt    NH   CO  Me                                 4.068.                                                                               CHiPr     1CH.sub.2  CHEt    NH   CO  Me                                 4.069.                                                                               CHcPr     0          CH.sub.2                                                                               NH   CO  Me                                 4.070.                                                                               CHcPr     1CH.sub.2  CH.sub.2                                                                               NH   CO  Me                                 4.071.                                                                               CHEt      0          CH.sub.2                                                                               NH   CO  Me                                 4.072.                                                                               CHEt      1CH.sub.2  CH.sub.2                                                                               NH   CO  Me                                 4.073.                                                                               CHEt      0          CH.sub.2                                                                               NH   CO  Me                                 4.074.                                                                               CHEt      1CH.sub.2  CH.sub.2                                                                               NH   CO  Me                                 4.075.                                                                               CHEt      0          CHMe    NH   CO  Me                                 4.076.                                                                               CHEt      1CH.sub.2  CHMe    NH   CO  Me                                 4.077.                                                                               CHEt      0          CHEt    NH   CO  Me                                 4.078.                                                                               CHEt      1CH.sub.2  CHEt    NH   CO  Me                                 4.079.                                                                               CMe.sub.2 0          CO      NH   CO  Me                                 4.080.                                                                               CMe.sub.2 1CH.sub.2  CO      NH   CO  Me                                 4.081.                                                                               CMe.sub.2 0          CH.sub.2                                                                               NH   CO  Me                                 4.082.                                                                               CMe.sub.2 1CH.sub.2  CH.sub.2                                                                               NH   CO  Me                                 4.083.                                                                               CMe       0          N       NH   CO  Me                                 4.084.                                                                               CHMe      1CH.sub.2  NH      NH   CO  Me                                 4.085.                                                                               CMe       0          CH      NH   CO  Me                                 4.086.                                                                               CHMe      1CH.sub.2  CH.sub.2                                                                               NH   CO  Me                                 4.101.                                                                               CO        1CMe.sub.2 CO      NH   CO  CF.sub.3                           4.102.                                                                               CO        1CMe.sub.2 CH.sub.2                                                                               NH   CO  CF.sub.3                           4.103.                                                                               CO        0          CH.sub.2                                                                               NH   CO  CF.sub.3                           4.104.                                                                               CO        1CH.sub.2  CH.sub.2                                                                               NH   CO  CF.sub.3                           4.105.                                                                               CO        0          CMe.sub.2                                                                              NH   CO  CF.sub.3                           4.106.                                                                               CO        1CH.sub.2  CMe.sub.2                                                                              NH   CO  CF.sub.3                           4.107.                                                                               CH.sub.2  1CMe.sub.2 CO      NH   CO  CF.sub.3                           4.108.                                                                               CH.sub.2  0          CO      NH   CO  CF.sub.3                           4.109.                                                                               CH.sub.2  1CH.sub.2  CO      NH   CO  CF.sub.3                           4.110.                                                                               CH.sub.2  0          CH.sub.2                                                                               NH   CO  CF.sub.3                           4.111.                                                                               CH.sub.2  1CH.sub.2  CH.sub.2                                                                               NH   CO  CF.sub.3                           4.112.                                                                               CH.sub.2  1CMe.sub.2 CH.sub.2                                                                               NH   CO  CF.sub.3                           4.113.                                                                               CH.sub.2  1CMe.sub.2 CH.sub.2                                                                               NH   CO  CF.sub.3                           4.114.                                                                               CH.sub.2  1C(OMe).sub.2                                                                             CH.sub.2                                                                               NH   CO  CF.sub.3                           4.115.                                                                               CH.sub.2  1C(OEt).sub.2                                                                             CH.sub.2                                                                               NH   CO  CF.sub.3                           4.116.                                                                               CH.sub.2  1C(CH.sub.2 OH).sub.2                                                                     CH.sub.2                                                                               NH   CO  CF.sub.3                           4.117.                                                                               CH.sub.2  1CO        CH.sub.2                                                                               NH   CO  CF.sub.3                           4.118.                                                                               CH.sub.2  1CHOH      CH.sub.2                                                                               NH   CO  CF.sub.3                           4.119.                                                                               CH.sub.2  1O         CH.sub.2                                                                               NH   CO  CF.sub.3                           4.120.                                                                               CH.sub.2  1NMe       CH.sub.2                                                                               NH   CO  CF.sub.3                           4.121.                                                                               CH.sub.2  0          CH.sub.2                                                                               NH   CO  CF.sub.3                           4.122.                                                                               CH.sub.2  1CH.sub.2  CH.sub.2                                                                               NH   CO  CF.sub.3                           4.123.                                                                               CH.sub.2  1CH.sub.2  CH.sub.2                                                                               NH   CO  CF.sub.3                           4.124.                                                                               CH.sub.2  1CH        CH      NH   CO  CF.sub.3                           4.125.                                                                               CH.sub.2  0          CHMe    NH   CO  CF.sub.3                           4.126.                                                                               CH.sub.2  0          CHMe    NH   CO  CF.sub.3                           4.127.                                                                               CH.sub.2  1CH.sub.2  CHMe    NH   CO  CF.sub.3                           4.128.                                                                               CH.sub.2  1CH.sub.2  CHMe    NH   CO  CF.sub.3                           4.129.                                                                               CH.sub.2  0          CHCH.sub.2 OMe                                                                         NH   CO  CF.sub.3                           4.130.                                                                               CH.sub.2  1CH.sub.2  CHCH.sub.2 OMe                                                                         NH   CO  CF.sub.3                           4.131.                                                                               CH.sub.2  0          CHtBu   NH   CO  CF.sub.3                           4.132.                                                                               CH.sub.2  1CH.sub.2  CHtBu   NH   CO  CF.sub.3                           4.133.                                                                               CH.sub.2  0          CHiPr   NH   CO  CF.sub.3                           4.134.                                                                               CH.sub.2  1CH.sub.2  CHiPr   NH   CO  CF.sub.3                           4.135.                                                                               CH.sub.2  0          CHcPr   NH   CO  CF.sub.3                           4.136.                                                                               CH.sub.2  1CH.sub.2  CHcPr   NH   CO  CF.sub.3                           4.137.                                                                               CH.sub.2  0          CHEt    NH   CO  CF.sub.3                           4.138.                                                                               CH.sub.2  0          CHEt    NH   CO  CF.sub.3                           4.139.                                                                               CH.sub.2  1CH.sub.2  CHEt    NH   CO  CF.sub.3                           4.140.                                                                               CH.sub.2  1CH.sub.2  CHEt    NH   CO  CF.sub.3                           4.141.                                                                               CH.sub.2  1CMe       CH      NH   CO  CF.sub.3                           4.142.                                                                               CH.sub.2  1CEt       CH      NH   CO  CF.sub.3                           4.143.                                                                               CH        0          N       NH   CO  CF.sub.3                           4.144.                                                                               CH        1CH.sub.2  N       NH   CO  CF.sub.3                           4.145.                                                                               CH        1CMe       CH.sub.2                                                                               NH   CO  CF.sub.3                           4.146.                                                                               CH        1CEt       CH.sub.2                                                                               NH   CO  CF.sub.3                           4.147.                                                                               CH        0          CMe     NH   CO  CF.sub.3                           4.148.                                                                               CH.sub.2  1CH.sub.2  CHMe    NH   CO  CF.sub.3                           4.149.                                                                               CHMe      0          CH.sub.2                                                                               NH   CO  CF.sub.3                           4.150.                                                                               CHMe      1CH        CH      NH   CO  CF.sub.3                           4.151.                                                                               CHMe      0          CH.sub.2                                                                               NH   CO  CF.sub.3                           4.152.                                                                               CHMe      1CH.sub.2  CH.sub.2                                                                               NH   CO  CF.sub.3                           4.153.                                                                               CHMe      0          CHMe    NH   CO  CF.sub.3                           4.154.                                                                               CHMe      1CH.sub.2  CHMe    NH   CO  CF.sub.3                           4.155.                                                                               CHMe      0          CHEt    NH   CO  CF.sub.3                           4.156.                                                                               CHMe      1CH.sub.2  CHEt    NH   CO  CF.sub.3                           4.157.                                                                               CHCH.sub.2 OMe                                                                           0          CH.sub.2                                                                               NH   CO  CF.sub.3                           4.158.                                                                               CHCH.sub.2 OMe                                                                           1CH.sub.2  CH.sub.2                                                                               NH   CO  CF.sub.3                           4.159.                                                                               CHtBu     0          CH.sub.2                                                                               NH   CO  CF.sub.3                           4.160.                                                                               CHtBu     1CH.sub.2  CH.sub.2                                                                               NH   CO  CF.sub.3                           4.161.                                                                               CHiPr     0          CH.sub.2                                                                               NH   CO  CF.sub.3                           4.162.                                                                               CHiPr     1CH.sub.2  CH.sub.2                                                                               NH   CO  CF.sub.3                           4.163.                                                                               CHiPr     0          CH.sub.2                                                                               NH   CO  CF.sub.3                           4.164.                                                                               CHiPr     1CH.sub.2  CH.sub.2                                                                               NH   CO  CF.sub.3                           4.165.                                                                               CHiPr     0          CHMe    NH   CO  CF.sub.3                           4.166.                                                                               CHiPr     1CH.sub.2  CHMe    NH   CO  CF.sub.3                           4.167.                                                                               CHiPr     0          CHEt    NH   CO  CF.sub.3                           4.168.                                                                               CHiPr     1CH.sub.2  CHEt    NH   CO  CF.sub.3                           4.169.                                                                               CHcPr     0          CH.sub.2                                                                               NH   CO  CF.sub.3                           4.170.                                                                               CHcPr     1CH.sub.2  CH.sub.2                                                                               NH   CO  CF.sub.3                           4.171.                                                                               CHEt      0          CH.sub.2                                                                               NH   CO  CF.sub.3                           4.172.                                                                               CHEt      1CH.sub.2  CH.sub.2                                                                               NH   CO  CF.sub.3                           4.173.                                                                               CHEt      0          CH.sub.2                                                                               NH   CO  CF.sub.3                           4.174.                                                                               CHEt      1CH.sub.2  CH.sub.2                                                                               NH   CO  CF.sub.3                           4.175.                                                                               CHEt      0          CHMe    NH   CO  CF.sub.3                           4.176.                                                                               CHEt      1CH.sub.2  CHMe    NH   CO  CF.sub.3                           4.177.                                                                               CHEt      0          CHEt    NH   CO  CF.sub.3                           4.178.                                                                               CHEt      1CH.sub.2  CHEt    NH   CO  CF.sub.3                           4.179.                                                                               CMe.sub.2 0          CO      NH   CO  CF.sub.3                           4.180.                                                                               CMe.sub.2 1CH.sub.2  CO      NH   CO  CF.sub.3                           4.181.                                                                               CMe.sub.2 0          CH.sub.2                                                                               NH   CO  CF.sub.3                           4.182.                                                                               CMe.sub.2 1CH.sub.2  CH.sub.2                                                                               NH   CO  CF.sub.3                           4.183.                                                                               CMe       0          N       NH   CO  CF.sub.3                           4.184.                                                                               CHMe      1CH.sub.2  NH      NH   CO  CF.sub.3                           4.185.                                                                               CMe       0          CH      NH   CO  CF.sub.3                           4.186.                                                                               CHMe      1CH.sub.2  CH.sub.2                                                                               NH   CO  CF.sub.3                           4.201.                                                                               CO        1CMe.sub.2 CO      NH   CO  Et                                 4.202.                                                                               CO        1CMe.sub.2 CH.sub.2                                                                               NH   CO  Et                                 4.203.                                                                               CO        0          CH.sub.2                                                                               NH   CO  Et                                 4.204.                                                                               CO        1CH.sub.2  CH.sub.2                                                                               NH   CO  Et                                 4.205.                                                                               CO        0          CMe.sub.2                                                                              NH   CO  Et                                 4.206.                                                                               CO        1CH.sub.2  CMe.sub.2                                                                              NH   CO  Et                                 4.207.                                                                               CH.sub.2  1CMe.sub.2 CO      NH   CO  Et                                 4.208.                                                                               CH.sub.2  0          CO      NH   CO  Et                                 4.209.                                                                               CH.sub.2  1CH.sub.2  CO      NH   CO  Et                                 4.210.                                                                               CH.sub.2  0          CH.sub.2                                                                               NH   CO  Et                                 4.211.                                                                               CH.sub.2  1CH.sub.2  CH.sub.2                                                                               NH   CO  Et                                 4.212.                                                                               CH.sub.2  1CMe.sub.2 CH.sub.2                                                                               NH   CO  Et                                 4.213.                                                                               CH.sub.2  1CMe.sub.2 CH.sub.2                                                                               NH   CO  Et                                 4.214.                                                                               CH.sub.2  1C(OMe).sub.2                                                                             CH.sub.2                                                                               NH   CO  Et                                 4.215.                                                                               CH.sub.2  1C(OEt).sub.2                                                                             CH.sub.2                                                                               NH   CO  Et                                 4.216.                                                                               CH.sub.2  1C(CH.sub.2 OH).sub.2                                                                     CH.sub.2                                                                               NH   CO  Et                                 4.217.                                                                               CH.sub.2  1CO        CH.sub.2                                                                               NH   CO  Et                                 4.218.                                                                               CH.sub.2  1CHOH      CH.sub.2                                                                               NH   CO  Et                                 4.219.                                                                               CH.sub.2  1O         CH.sub.2                                                                               NH   CO  Et                                 4.220.                                                                               CH.sub.2  1NMe       CH.sub.2                                                                               NH   CO  Et                                 4.221.                                                                               CH.sub.2  0          CH.sub.2                                                                               NH   CO  Et                                 4.222.                                                                               CH.sub.2  1CH.sub.2  CH.sub.2                                                                               NH   CO  Et                                 4.223.                                                                               CH.sub.2  1CH.sub.2  CH.sub.2                                                                               NH   CO  Et                                 4.224.                                                                               CH.sub.2  1CH        CH      NH   CO  Et                                 4.225.                                                                               CH.sub.2  0          CHMe    NH   CO  Et                                 4.226.                                                                               CH.sub.2  0          CHMe    NH   CO  Et                                 4.227.                                                                               CH.sub.2  1CH.sub.2  CHMe    NH   CO  Et                                 4.228.                                                                               CH.sub.2  1CH.sub.2  CHMe    NH   CO  Et                                 4.229.                                                                               CH.sub.2  0          CHCH.sub.2 OMe                                                                         NH   CO  Et                                 4.230.                                                                               CH.sub.2  1CH.sub.2  CHCH.sub.2 OMe                                                                         NH   CO  Et                                 4.231.                                                                               CH.sub.2  0          CHtBu   NH   CO  Et                                 4.232.                                                                               CH.sub.2  1CH.sub.2  CHtBu   NH   CO  Et                                 4.233.                                                                               CH.sub.2  0          CHiPr   NH   CO  Et                                 4.234.                                                                               CH.sub.2  1CH.sub.2  CHiPr   NH   CO  Et                                 4.235.                                                                               CH.sub.2  0          CHcPr   NH   CO  Et                                 4.236.                                                                               CH.sub.2  1CH.sub.2  CHcPr   NH   CO  Et                                 4.237.                                                                               CH.sub.2  0          CHEt    NH   CO  Et                                 4.238.                                                                               CH.sub.2  0          CHEt    NH   CO  Et                                 4.239.                                                                               CH.sub.2  1CH.sub.2  CHEt    NH   CO  Et                                 4.240.                                                                               CH.sub.2  1CH.sub.2  CHEt    NH   CO  Et                                 4.241.                                                                               CH.sub.2  1CMe       CH      NH   CO  Et                                 4.242.                                                                               CH.sub.2  1CEt       CH      NH   CO  Et                                 4.243.                                                                               CH        0          N       NH   CO  Et                                 4.244.                                                                               CH        1CH.sub.2  N       NH   CO  Et                                 4.245.                                                                               CH        1CMe       CH.sub.2                                                                               NH   CO  Et                                 4.246.                                                                               CH        1CEt       CH.sub.2                                                                               NH   CO  Et                                 4.247.                                                                               CH        0          CMe     NH   CO  Et                                 4.248.                                                                               CH.sub.2  1CH.sub.2  CHMe    NH   CO  Et                                 4.249.                                                                               CHMe      0          CH.sub.2                                                                               NH   CO  Et                                 4.250.                                                                               CHMe      1CH        CH      NH   CO  Et                                 4.248.                                                                               CH        1CH.sub.2  CMe     NH   CO  Et                                 4.249.                                                                               CHMe      0          CH      NH   CO  Et                                 4.250.                                                                               CHMe      1CH.sub.2  CH      NH   CO  Et                                 4.251.                                                                               CHMe      0          CH.sub.2                                                                               NH   CO  Et                                 4.252.                                                                               CHMe      1CH.sub.2  CH.sub.2                                                                               NH   CO  Et                                 4.253.                                                                               CHMe      0          CHMe    NH   CO  Et                                 4.254.                                                                               CHMe      1CH.sub.2  CHMe    NH   CO  Et                                 4.255.                                                                               CHMe      0          CHEt    NH   CO  Et                                 4.256.                                                                               CHMe      1CH.sub.2  CHEt    NH   CO  Et                                 4.257.                                                                               CHCH.sub.2 OMe                                                                           0          CH.sub.2                                                                               NH   CO  Et                                 4.258.                                                                               CHCH.sub.2 OMe                                                                           1CH.sub.2  CH.sub.2                                                                               NH   CO  Et                                 4.259.                                                                               CHtBu     0          CH.sub.2                                                                               NH   CO  Et                                 4.260.                                                                               CHtBu     1CH.sub.2  CH.sub.2                                                                               NH   CO  Et                                 4.261.                                                                               CHiPr     0          CH.sub.2                                                                               NH   CO  Et                                 4.262.                                                                               CHiPr     1CH.sub.2  CH.sub.2                                                                               NH   CO  Et                                 4.263.                                                                               CHiPr     0          CH.sub.2                                                                               NH   CO  Et                                 4.264.                                                                               CHiPr     1CH.sub.2  CH.sub.2                                                                               NH   CO  Et                                 4.265.                                                                               CHiPr     0          CHMe    NH   CO  Et                                 4.266.                                                                               CHiPr     1CH.sub.2  CHMe    NH   CO  Et                                 4.267.                                                                               CHiPr     0          CHEt    NH   CO  Et                                 4.268.                                                                               CHiPr     1CH.sub.2  CHEt    NH   CO  Et                                 4.269.                                                                               CHcPr     0          CH.sub.2                                                                               NH   CO  Et                                 4.270.                                                                               1CH.sub.2 CH.sub.2   NH      CO   Et                                     4.271.                                                                               CHEt      0          CH.sub.2                                                                               NH   CO  Et                                 4.272.                                                                               CHEt      1CH.sub.2  CH.sub.2                                                                               NH   CO  Et                                 4.273.                                                                               CHEt      0          CH.sub.2                                                                               NH   CO  Et                                 4.274.                                                                               CHEt      1CH.sub.2  CH.sub.2                                                                               NH   CO  Et                                 4.275.                                                                               CHEt      0          CHMe    NH   CO  Et                                 4.276.                                                                               CHEt      1CH.sub.2  CHMe    NH   CO  Et                                 4.277.                                                                               CHEt      0          CHEt    NH   CO  Et                                 4.278.                                                                               CHEt      1CH.sub.2  CHEt    NH   CO  Et                                 4.279.                                                                               CMe.sub.2 0          CO      NH   CO  Et                                 4.280.                                                                               CMe.sub.2 1CH.sub.2  CO      NH   CO  Et                                 4.281.                                                                               CMe.sub.2 0          CH.sub.2                                                                               NH   CO  Et                                 4.282.                                                                               CMe.sub.2 1CH.sub.2  CH.sub.2                                                                               NH   CO  Et                                 4.283.                                                                               CMe       0          N       NH   CO  Et                                 4.284.                                                                               CHMe      1CH.sub.2  NH      NH   CO  Et                                 4.285.                                                                               CMe       0          CH      NH   CO  Et                                 4.286.                                                                               CHMe      1CH.sub.2  CH.sub.2                                                                               NH   CO  Et                                 ______________________________________                                    

                  TABLE 4a                                                         ______________________________________                                         (melting points of compounds from Table 4)                                            Comp. m.p.(°)                                                    ______________________________________                                                4.025 124-127                                                                  4.047 198-201                                                           ______________________________________                                    

EXAMPLE P21 1,3-Bis(pyridin-3-ylmethyleneamino)urea

32.2 g of pyridine-3-carbaldehyde are added in the course of approx. 10 minutes, at room temperature, to a suspension of 13.5 g of carbohydrazide in 200 ml of methanol, the temperature rising to more than 35°. The reaction mixture is further stirred for 1 hour and then cooled to 5°. The crystals that precipitate are filtered off with suction and dried in vacuo at 70°. 40 g of the title compound having a melting point of 202°-204° are thus obtained.

EXAMPLE P22 1,3-Bis(pyridin-3-ylmethyleneamino)4-hydroxy-4-methylimidazolidin-2-one (Compound 5.100 in Table 5)

27.6 g of potassium carbonate and 13.9 g of chloroacetone are added to a solution of 26.8 g of 1,3-bis(pyridin-3-ylmethyleneamino)urea in 300 ml of dimethylformamide. When the slightly exothermic reaction has subsided, stirring is continued for about 1 hour. 500 ml of ether are added to the resulting suspension. The suspension is then filtered and the crystals are dried. 58 g of a crystal mixture are obtained. 200 ml of methylene chloride and 50 ml of water are added to the crystal mixture, which is then stirred for 30 minutes. The remaining crystals are filtered off with suction, washed with methylene chloride and water (1:1) and dried in vacuo at 70°. 25.3 g of the title compound having a melting point of 175°-182° are thus obtained.

EXAMPLE P23 1,3-Bis(pyridin-3-ylmethyleneamino)-4-methyl-1,3-dihydroimidazol-2-one (Compound 5.096 in Table 5) and 1,3-bis(pyridin-3-ylmethyleneamino)-4-methoxy-4-methylimidazolidin-2-one (Compound 5.110 in Table 5)

Concentrated sulfuric acid is added dropwise to a suspension of 9.8 g of 1,3-bis(pyridin-3-ylmethyleneamino)4-hydroxy-4-methylimidazolidin-2-one in 20 ml of methanol. When the reaction mixture, the temperature of which rises quickly, becomes difficult to stir, a further 20 ml of methanol are added and then further sulfuric acid is added dropwise. When the reaction mixture, the temperature of which continues to rise quickly, again becomes difficult to stir, a further 20 ml of methanol are added and then further sulfuric acid is added dropwise (approx. 4 ml in total). The reaction mixture is cooled to 20°, filtered with suction, washed with methanol and dried. 8.8 g of crystals of the disulfate of 1,3-bis(pyridin-3-ylmethyleneamino)-4-methyl-1,3-dihydroimidazol-2-one having a melting point of 202°-205° are obtained.

The mother liquor is chromatographed on silica gel with ether/tetrahydrofuran, there being obtained inter alia 0.55 g of crystals of 1,3-bis(pyridin-3-ylmethyleneamino)-4-methoxy-4-methylimidazolidin-2-one having a melting point of 202°-207°.

7.7 g of the disulfate of 1,3-bis(pyridin-3-ylmethyleneamino)-4-methyl-1,3-dihydroimidazol-2-one are dissolved in 200 ml of water. The pH is brought to 7 with 2N sodium hydroxide solution, whereupon crystals precipitate. The crystals are extracted four times with 100 ml of methylene chloride each time. The organic phase is dried with magnesium sulfate and concentrated by evaporation. The residue is stirred with ether, filtered with suction and dried. 4.1 g of crystals of 1,3-bis(pyridin-3-ylmethyleneamino)-4-methyl-1,3-dihydroimidazol-2-one having a melting point of 172°-174° are thus obtained.

EXAMPLE P24 1,3-Bis(pyridin-3-ylmethyleneamino)-4-methyl-1,3-dihydroimidazol-2-one (Compound 5.096 in Table 5)

11.2 g of acetic anhydride are added to a suspension of 32.4 g of 1,3-bis(pyridin-3-ylmethyleneamino)-4-hydroxy-4-methylimidazolidin-2-one in 75 ml of acetic acid. The reaction mixture is then heated to 50°. After 3 hours the reaction mixture is cooled to 20°, then poured onto 800 ml of ice-water and neutralised with 30% sodium hydroxide solution. The aqueous phase is then extracted three times with 200 ml of methylene chloride each time. The organic phase is dried with magnesium sulfate, filtered and concentrated by evaporation. The residue is stirred with ether. The crystals are filtered off with suction and dried. 28.2 g of the title compound having a melting point of 176°-178° are thus obtained.

EXAMPLE P25

The other compounds listed in Tables 5, 5a and 6 can also be prepared in a manner analogous to that described in Examples P21 to P24.

                                      TABLE 5                                      __________________________________________________________________________      ##STR24##                                                                     No. A        m B        D         G                                            __________________________________________________________________________     5.001                                                                              CO       1 NCH.sub.2 cHex                                                                          CO        CO                                           5.002                                                                              CO       1 CH.sub.2 CO        CO                                           5.003                                                                              CO       1 CMe.sub.2                                                                               CO        CO                                           5.004                                                                              CO       0          CO        CO                                           5.005                                                                              CO       1 CH.sub.2 CH.sub.2  CO                                           5.006                                                                              CO       1 CMe.sub.2                                                                               CH.sub.2  CO                                           5.007                                                                              CO       0          CH.sub.2  CO                                           5.008                                                                              CO       0          CHCH.sub.2 COOMe                                                                         CS                                           5.009                                                                              CO       0          CHC.sub.2 H.sub.4 COOMe                                                                  CS                                           5.010                                                                              CO       1 CH.sub.2 CMe.sub.2 CO                                           5.011                                                                              CO       0          CMe.sub.2 CO                                           5.012                                                                              CO       1 CH       CMe       CO                                           5.013                                                                              CO       0          CMeCH.sub.2 CMe.sub.2                                                                    CO                                           5.014                                                                              CO       0          CMeCHCMe.sub.2                                                                           CO                                           5.015                                                                              CO       1 CH       CCF.sub.3 CNH                                          5.016                                                                              CH.sub.2 0          CO        CO                                           5.017                                                                              CH.sub.2 0          CO        CS                                           5.018                                                                              CH.sub.2 1 CMe.sub.2                                                                               CO        CO                                           5.019                                                                              CH.sub.2 0          CO        CO                                           5.020                                                                              CH.sub.2 1 CH.sub.2 CO        CO                                           5.021                                                                              CH.sub.2 0          CH.sub.2  CO                                           5.022                                                                              CH.sub.2 0          CH.sub.2  CS                                           5.023                                                                              CH.sub.2 0          CH.sub.2  CO                                           5.024                                                                              CH.sub.2 0          CH.sub.2  CO                                           5.025                                                                              CH.sub.2 1 CH.sub.2 CH.sub.2  CO                                           5.026                                                                              CH.sub.2 1 CMe.sub.2                                                                               CH.sub.2  CO                                           5.027                                                                              CH.sub.2 1 CMe.sub.2                                                                               CH.sub.2  CO                                           5.028                                                                              CH.sub.2 1 C(OMe).sub.2                                                                            CH.sub.2  CO                                           5.029                                                                              CH.sub.2 1 C(OEt).sub.2                                                                            CH.sub.2  CO                                           5.030                                                                              CH.sub.2 1 C(CH.sub.2 OH).sub.2                                                                    CH.sub.2  CO                                           5.031                                                                              CH.sub.2 1 CO       CH.sub.2  CO                                           5.032                                                                              CH.sub.2 1 CHOH     CH.sub.2  CO                                           5.033                                                                              CH.sub.2 1 O        CH.sub.2  CO                                           5.034                                                                              CH.sub.2 1 NMe      CH.sub.2  CO                                           5.035                                                                              CH.sub.2 0          CH.sub.2  CO                                           5.036                                                                              CH.sub.2 1 CH.sub.2 CH.sub.2  CO                                           5.037                                                                              CH.sub.2 1 CH.sub.2 CH.sub.2  CO                                           5.038                                                                              CH.sub.2 1 CH       CH        CO                                           5.039                                                                              CH.sub.2 0          CHMe      CO                                           5.040                                                                              CH.sub.2 0          CHMe      CO                                           5.041                                                                              CH.sub.2 1 CH.sub.2 CHMe      CO                                           5.042                                                                              CH.sub.2 1 CH.sub.2 CHMe      CO                                           5.043                                                                              CH.sub.2 0          CHCH.sub.2 OMe                                                                           CO                                           5.044                                                                              CH.sub.2 1 CH.sub.2 CHCH.sub.2 OMe                                                                           CO                                           5.045                                                                              CH.sub.2 0          CHtBu     CO                                           5.046                                                                              CH.sub.2 1 CH.sub.2 CHtBu     CO                                           5.047                                                                              CH.sub.2 0          CHiPr     CO                                           5.048                                                                              CH.sub.2 1 CH.sub.2 CHiPr     CO                                           5.049                                                                              CH.sub.2 0          CHcPr     CO                                           5.050                                                                              CH.sub.2 1 CH.sub.2 CHcPr     CO                                           5.051                                                                              CH.sub.2 0          CHEt      CO                                           5.052                                                                              CH.sub.2 0          CHEt      CO                                           5.053                                                                              CH.sub.2 1 CH.sub.2 CHEt      CO                                           5.054                                                                              CH.sub.2 1 CH.sub.2 CHEt      CO                                           5.055                                                                              CH.sub.2 1 CMe      CH        CO                                           5.056                                                                              CH.sub.2 1 CEt      CH        CO                                           5.057                                                                              CH       1 CMe      CH.sub.2  CO                                           5.058                                                                              CH       1 CEt      CH.sub.2  CO                                           5.059                                                                              CH       0          CMe       CO                                           5.060                                                                              CH       1 CH.sub.2 CMe       CO                                           5.061                                                                              CH       0          CtBu      CO                                           5.062                                                                              CHMe     0          CHnPr     CO                                           5.063                                                                              CHMe     1 CH.sub.2 CHnPr     CO                                           5.064                                                                              CHMe     0          CH.sub.2  CO                                           5.065                                                                              CHMe     1 CH.sub.2 CH.sub.2  CO                                           5.066                                                                              CHMe     0          CHMe      CO                                           5.067                                                                              CHMe     1 CH.sub.2 CHMe      CO                                           5.068                                                                              CHMe     0          CHEt      CO                                           5.069                                                                              CHMe     1 CH.sub.2 CHEt      CO                                           5.070                                                                              CHCH.sub.2 OMe                                                                          0          CH.sub.2  CO                                           5.071                                                                              CHCH.sub.2 OMe                                                                          1 CH.sub.2 CH.sub.2  CO                                           5.072                                                                              CHtBu    0          CH.sub.2  CO                                           5.073                                                                              CHtBu    1 CH.sub.2 CH.sub.2  CO                                           5.074                                                                              CHiPr    0          CH.sub.2  CO                                           5.075                                                                              CHiPr    1 CH.sub.2 CH.sub.2  CO                                           5.076                                                                              CHiPr    0          CH.sub.2  CO                                           5.077                                                                              CHiPr    1 CH.sub.2 CH.sub.2  CO                                           5.078                                                                              CHiPr    0          CHMe      CO                                           5.079                                                                              CHiPr    1 CH.sub.2 CHMe      CO                                           5.080                                                                              CHiPr    0          CHEt      CO                                           5.081                                                                              CHiPr    1 CH.sub.2 CHEt      CO                                           5.082                                                                              CHcPr    0          CH.sub.2  CO                                           5.083                                                                              CHcPr    1 CH.sub.2 CH.sub.2  CO                                           5.084                                                                              CHEt     0          CH.sub.2  CO                                           5.085                                                                              CHEt     1 CH.sub.2 CH.sub.2  CO                                           5.086                                                                              CHEt     0          CH.sub.2  CO                                           5.087                                                                              CHEt     1 CH.sub.2 CH.sub.2  CO                                           5.088                                                                              CHEt     0          CHMe      CO                                           5.089                                                                              CHEt     1 CH.sub.2 CHMe      CO                                           5.090                                                                              CHEt     0          CHEt      CO                                           5.091                                                                              CHEt     1 CH.sub.2 CHEt      CO                                           5.092                                                                              CMe.sub.2                                                                               0          CO        CO                                           5.093                                                                              CMe.sub.2                                                                               1 CH.sub.2 CO        CO                                           5.094                                                                              CMe.sub.2                                                                               0          CH.sub.2  CO                                           5.095                                                                              CMe.sub.2                                                                               1 CH.sub.2 CH.sub.2  CO                                           5.096                                                                              CMe      0          CH        CO                                           5.097                                                                              CMe      1 CH.sub.2 CH        CO                                           5.098                                                                              C(NH)    0          CMe.sub.2 CO                                           5.099                                                                              C(NH)    1 CH       CMe       CO                                           5.100                                                                              C(OH)Me  0          CH.sub.2  CO                                           5.101                                                                              C(OH)Et  0          CH.sub.2  CO                                           5.102                                                                              C(OH)iPr 0          CH.sub.2  CO                                           5.103                                                                              C(OH)cPr 0          CH.sub.2  CO                                           5.104                                                                              C(OH)Et  1 CH.sub.2 CH.sub.2  CO                                           5.105                                                                              C(OH)iPr 1 CH.sub.2 CH.sub.2  CO                                           5.106                                                                              C(OH)cPr 1 CH.sub.2 CH.sub.2  CO                                           5.107                                                                              C(OH)Me  1 CHMe     CH.sub.2  CO                                           5.108                                                                              CHOH     1 CHMe     CH.sub.2  CO                                           5.109                                                                              C(OEt)Me 0          CH.sub.2  CO                                           5.110                                                                              C(OMe)Me 0          CH.sub.2  CO                                           5.111                                                                              C(OH)Me  0          CHMe      CO                                           5.112                                                                              CH.sub.2 1 CH(COOMe)                                                                               CH.sub.2  CO                                           5.113                                                                              C(Me)    0          C(Me)     CO                                           __________________________________________________________________________

                  TABLE 5a                                                         ______________________________________                                         (melting points of compounds from Table 4)                                     Comp.                m.p.(°)                                            ______________________________________                                         5.023                >240                                                      5.025                218-219                                                   5.036                218-219                                                   5.059                176-178                                                   5.096                176-178                                                   5.100                175-182                                                   5.110                202-207                                                   5.111                152-154                                                   5.112                208-209                                                   5.113                203                                                       ______________________________________                                    

                                      TABLE 6                                      __________________________________________________________________________      ##STR25##                                                                     No. A      m B      D        G   m.p.                                          __________________________________________________________________________     6.001.                                                                             CO     1 N(CH.sub.2 cHex)                                                                      CO       CO                                                6.002.                                                                             CO     1 CH.sub.2                                                                              CO       CO                                                6.003.                                                                             CO     1 CMe.sub.2                                                                             CO       CO                                                6.004.                                                                             CO     0        CO       CO                                                6.005.                                                                             CO     1 CH.sub.2                                                                              CH.sub.2 CO                                                6.006.                                                                             CO     1 CMe.sub.2                                                                             CH.sub.2 CO                                                6.007.                                                                             CO     0        CH.sub.2 CO                                                6.008.                                                                             CO     0        CHCH.sub.2 COOMe                                                                        CS                                                6.009.                                                                             CO     0        CHC.sub.2 H.sub.4 COOMe                                                                 CS                                                6.010.                                                                             CO     1 CH.sub.2                                                                              CMe.sub.2                                                                               CO                                                6.011.                                                                             CO     0        CMe.sub.2                                                                               CO                                                6.012.                                                                             CO     1 CH     CMe      CO                                                6.013.                                                                             CO     0        CMeCH.sub.2 CMe.sub.2                                                                   CO                                                6.014.                                                                             CO     0        CMeCHCMe.sub.2                                                                          CO                                                6.015.                                                                             CO     1 CH     CCF.sub.3                                                                               CNH                                               6.016.                                                                             CH.sub.2                                                                              0        CO       CO                                                6.017.                                                                             CH.sub.2                                                                              0        CO       CS                                                6.018.                                                                             CH.sub.2                                                                              1 CMe.sub.2                                                                             CO       CO                                                6.019.                                                                             CH.sub.2                                                                              0        CO       CO                                                6.020.                                                                             CH.sub.2                                                                              1 CH.sub.2                                                                              CO       CO                                                6.021.                                                                             CH.sub.2                                                                              0        CH.sub.2 CO                                                6.022.                                                                             CH.sub.2                                                                              0        CH.sub.2 CS                                                6.023.                                                                             CH.sub.2                                                                              0        CH.sub.2 CO                                                6.024.                                                                             CH.sub.2                                                                              0        CH.sub.2 CO                                                6.025.                                                                             CH.sub.2                                                                              1 CH.sub.2                                                                              CH.sub.2 CO                                                6.026.                                                                             CH.sub.2                                                                              1 CMe.sub.2                                                                             CH.sub.2 CO                                                6.027.                                                                             CH.sub.2                                                                              1 CMe.sub.2                                                                             CH.sub.2 CO                                                6.028.                                                                             CH.sub.2                                                                              1 C(OMe).sub.2                                                                          CH.sub.2 CO                                                6.029.                                                                             CH.sub.2                                                                              1 C(OEt).sub.2                                                                          CH.sub.2 CO                                                6.030.                                                                             CH.sub.2                                                                              1 C(CH.sub.2 OH).sub.2                                                                  CH.sub.2 CO                                                6.031.                                                                             CH.sub.2                                                                              1 CO     CH.sub.2 CO                                                6.032.                                                                             CH.sub.2                                                                              1 CHOH   CH.sub.2 CO                                                6.033.                                                                             CH.sub.2                                                                              1 O      CH.sub.2 CO                                                6.034.                                                                             CH.sub.2                                                                              1 NMe    CH.sub.2 CO                                                6.035.                                                                             CH.sub.2                                                                              0        CH.sub.2 CO                                                6.036.                                                                             CH.sub.2                                                                              1 CH.sub.2                                                                              CH.sub.2 CO                                                6.037.                                                                             CH.sub.2                                                                              1 CH.sub.2                                                                              CH.sub.2 CO                                                6.038.                                                                             CH.sub.2                                                                              1 CH     CH       CO                                                6.039.                                                                             CH.sub.2                                                                              0        CHMe     CO                                                6.040.                                                                             CH.sub.2                                                                              0        CHMe     CO                                                6.041.                                                                             CH.sub.2                                                                              1 CH.sub.2                                                                              CHMe     CO                                                6.042.                                                                             CH.sub.2                                                                              1 CH.sub.2                                                                              CHMe     CO                                                6.043.                                                                             CH.sub.2                                                                              0        CHCH.sub.2 OMe                                                                          CO                                                6.044.                                                                             CH.sub.2                                                                              1 CH.sub.2                                                                              CHCH.sub.2 OMe                                                                          CO                                                6.045.                                                                             CH.sub.2                                                                              0        CHtBu    CO                                                6.046.                                                                             CH.sub.2                                                                              1 CH.sub.2                                                                              CHtBu    CO                                                6.047.                                                                             CH.sub.2                                                                              0        CHiPr    CO                                                6.048.                                                                             CH.sub.2                                                                              1 CH.sub.2                                                                              CHiPr    CO                                                6.049.                                                                             CH.sub.2                                                                              0        CHcPr    CO                                                6.050.                                                                             CH.sub.2                                                                              1 CH.sub.2                                                                              CHcPr    CO                                                6.051.                                                                             CH.sub.2                                                                              0        CHEt     CO                                                6.052.                                                                             CH.sub.2                                                                              0        CHEt     CO                                                6.053.                                                                             CH.sub.2                                                                              1 CH.sub.2                                                                              CHEt     CO                                                6.054.                                                                             CH.sub.2                                                                              1 CH.sub.2                                                                              CHEt     CO                                                6.055.                                                                             CH.sub.2                                                                              1 CMe    CH       CO                                                6.056.                                                                             CH.sub.2                                                                              1 CEt    CH       CO                                                6.057.                                                                             CH     1 CMe    CH.sub.2 CO                                                6.058.                                                                             CH     1 CEt    CH.sub.2 CO                                                6.059.                                                                             CH     0        CMe      CO                                                6.060.                                                                             CH     1 CH.sub.2                                                                              CMe      CO                                                6.061.                                                                             CH     0        CtBu     CO                                                6.061.                                                                             CH     0        CHtBu    CO                                                6.062.                                                                             CHMe   0        CHnPr    CO                                                6.063.                                                                             CHMe   1 CH.sub.2                                                                              CHnPr    CO                                                6.064.                                                                             CHMe   0        CH.sub.2 CO                                                6.065.                                                                             CHMe   1 CH.sub.2                                                                              CH.sub.2 CO                                                6.066.                                                                             CHMe   0        CHMe     CO                                                6.067.                                                                             CHMe   1 CH.sub.2                                                                              CHMe     CO                                                6.068.                                                                             CHMe   0        CHEt     CO                                                6.069.                                                                             CHMe   1 CH.sub.2                                                                              CHEt     CO                                                6.070.                                                                             CHCH.sub.2 OMe                                                                        0        CH.sub.2 CO                                                6.071.                                                                             CHCH.sub.2 OMe                                                                        1 CH.sub.2                                                                              CH.sub.2 CO                                                6.072.                                                                             CHtBu  0        CH.sub.2 CO                                                6.073.                                                                             CHtBu  1 CH.sub.2                                                                              CH.sub.2 CO                                                6.074.                                                                             CHiPr  0        CH.sub.2 CO                                                6.075.                                                                             CHiPr  1 CH.sub.2                                                                              CH.sub.2 CO                                                6.076.                                                                             CHiPr  0        CH.sub.2 CO                                                6.077.                                                                             CHiPr  1 CH.sub.2                                                                              CH.sub.2 CO                                                6.078.                                                                             CHiPr  0        CHMe     CO                                                6.079.                                                                             CHiPr  1 CH.sub.2                                                                              CHMe     CO                                                6.080.                                                                             CHiPr  0        CHEt     CO                                                6.081.                                                                             CHiPr  1 CH.sub.2                                                                              CHEt     CO                                                6.082.                                                                             CHcPr  0        CH.sub.2 CO                                                6.083.                                                                             CHcPr  1 CH.sub.2                                                                              CH.sub.2 CO                                                6.084.                                                                             CHEt   0        CH.sub.2 CO                                                6.085.                                                                             CHEt   1 CH.sub.2                                                                              CH.sub.2 CO                                                6.086.                                                                             CHEt   0        CH.sub.2 CO                                                6.087.                                                                             CHEt   1 CH.sub.2                                                                              CH.sub.2 CO                                                6.088.                                                                             CHEt   0        CHMe     CO                                                6.089.                                                                             CHEt   1 CH.sub.2                                                                              CHMe     CO                                                6.090.                                                                             CHEt   0        CHEt     CO                                                6.091.                                                                             CHEt   1 CH.sub.2                                                                              CHEt     CO                                                6.092.                                                                             CMe.sub.2                                                                             0        CO       CO                                                6.093.                                                                             CMe.sub.2                                                                             1 CH.sub.2                                                                              CO       CO                                                6.094.                                                                             CMe.sub.2                                                                             0        CH.sub.2 CO                                                6.095.                                                                             CMe.sub.2                                                                             1 CH.sub.2                                                                              CH.sub.2 CO                                                6.096.                                                                             CMe    0        CH       CO  148-150°                               6.097.                                                                             CMe    1 CH.sub.2                                                                              CH       CO                                                6.098.                                                                             C(NH)  0        CMe.sub.2                                                                               CO                                                6.099.                                                                             C(NH)  1 CH     CMe      CO                                                6.099.                                                                             C(NH)  1 CH     CMe      CO                                                6.100.                                                                             C(OH)Me                                                                               0        CH.sub.2 CO  175-176°                               6.101.                                                                             C(OH)Et                                                                               0        CH.sub.2 CO                                                6.102.                                                                             C(OH)iPr                                                                              0        CH.sub.2 CO                                                6.103.                                                                             C(OH)cPr                                                                              0        CH.sub.2 CO                                                6.104.                                                                             C(OH)Et                                                                               1 CH.sub.2                                                                              CH.sub.2 CO                                                6.105.                                                                             C(OH)iPr                                                                              1 CH.sub.2                                                                              CH.sub.2 CO                                                6.106.                                                                             C(OH)cPr                                                                              1 CH.sub.2                                                                              CH.sub.2 CO                                                6.107.                                                                             C(OH)Me                                                                               1 CHMe   CH.sub.2 CO                                                6.108.                                                                             CHOH   1 CHMe   CH.sub.2 CO                                                6.109.                                                                             C(OEt)Me                                                                              0        CH.sub.2 CO                                                6.110.                                                                             C(OMe)Me                                                                              0        CH.sub.2 CO                                                __________________________________________________________________________

EXAMPLE P26 3-(2-Cyclopropyl-2-oxo-ethyl)-5-methoxy-3H- 1,3,4!thiadiazol-2-one (Compound 7.055 in Table 7)

55 g of potassium carbonate are added to a solution of 26.4 g of 5-methoxy-3H- 1,3,4!-thiadiazol-2-one in 700 ml of dioxane and the reaction mixture is heated to 60°. Then 35 g of bromomethyl cyclopropyl ketone are added dropwise within a short period of time and the reaction mixture is stirred at 70° for 20 hours and then, at 20°, is filtered over Celite. The filtrate is concentrated by evaporation. The residue is stirred with diisopropyl ether and filtered with suction. 41 g of crystals of the title compound having a melting point of 98°-100° are thus obtained.

EXAMPLE P27 5-Methoxy-3-(2-oxopropyl)-3H- 1,3,4!thiadiazol-2-one (Compound 7.001 in Table 7)

69 g of potassium carbonate are added to a solution of 33 g of 5-methoxy-3H- 1,3,4!thiadiazol-2-one in 400 ml of dioxane and the reaction mixture is heated to 60°. Then 21 g of chloroacetone are added dropwise within a short period of time and the reaction mixture is stirred at 70° for 20 hours and then, at 20°, is filtered over Celite. The filtrate is concentrated by evaporation. The residue is stirred with diisopropyl ether and filtered with suction. 45 g of crystals of the title compound having a melting point of 66°-67° are thus obtained.

EXAMPLE P28 5-Methoxy-3-(1-ethoxy-2-oxopropyl)-3H- 1,3,4! thiadiazol-2-one (Compound 7.073 in Table 7)

69 g of potassium carbonate are added to a solution of 33 g of 5-methoxy-3H- 1,3,4!thiadiazol-2-one in 400 ml of dioxane and the reaction mixture is heated to 60°. Then 31 g of 1-chloro-3-ethoxypropan-2-one are added dropwise within a short period of time and the reaction mixture is stirred at 70° for 20 hours and then, at 20°, is filtered over Celite. The filtrate is concentrated by evaporation. 45 g of the title compound are thus obtained in the form of a light yellow oil.

EXAMPLE P29

The other compounds listed in Table 7 can also be prepared in a manner analogous to that described in Examples P26 and P28.

                  TABLE 7                                                          ______________________________________                                          ##STR26##                                                                     No.     R      R.sub.1  R.sub.2                                                                             R.sub.6    m.p.                                   ______________________________________                                         7.001   Me     H        H    Me         64-65°                          7.002   Et     H        H    Me                                                7.003   nPr    H        H    Me                                                7.004   Me     Me       H    Me         oil                                    7.005   Et     Me       H    Me                                                7.006   nPr    Me       H    Me                                                7.007   Me     Me       Me   Me                                                7.008   Et     Me       Me   Me                                                7.009   nPr    Me       Me   Me                                                7.010   Me     H        H    Et                                                7.011   Et     H        H    Et                                                7.012   nPr    H        H    Et                                                7.013   Me     Me       H    Et                                                7.014   Et     Me       H    Et                                                7.015   nPr    Me       H    Et                                                7.016   Me     Me       Me   Et                                                7.017   Et     Me       Me   Et                                                7.018   nPr    Me       Me   Et                                                7.019   Me     H        H    nPr                                               7.020   Et     H        H    nPr                                               7.021   nPr    H        H    nPr                                               7.022   Me     Me       H    nPr                                               7.023   Et     Me       H    nPr                                               7.024   nPr    Me       H    nPr                                               7.025   Me     Me       Me   nPr                                               7.026   Et     Me       Me   nPr                                               7.027   nPr    Me       Me   nPr                                               7.028   Me     H        H    nBu        oil                                    7.029   Et     H        H    nBu                                               7.030   nPr    H        H    nBu                                               7.031   Me     Me       H    nBu                                               7.032   Et     Me       H    nBu                                               7.033   nPr    Me       H    nBu                                               7.034   Me     Me       Me   nBu                                               7.035   Et     Me       Me   nBu                                               7.036   nPr    Me       Me   nBu                                               7.037   Me     H        H    iPr                                               7.038   Et     H        H    iPr                                               7.039   nPr    H        H    iPr                                               7.040   Me     Me       H    iPr                                               7.041   Et     Me       H    iPr                                               7.042   nPr    Me       H    iPr                                               7.043   Me     Me       Me   iPr                                               7.044   Et     Me       Me   iPr                                               7.045   nPr    Me       Me   iPr                                               7.046   Me     H        H    tBu        oil                                    7.047   Et     H        H    tBu                                               7.048   nPr    H        H    tBu                                               7.049   Me     Me       H    tBu                                               7.050   Et     Me       H    tBu                                               7.051   nPr    Me       H    tBu                                               7.052   Me     Me       Me   tBu                                               7.053   Et     Me       Me   tBu                                               7.054   nPr    Me       Me   tBu                                               7.055   Me     H        H    cPr         98-100°                        7.056   Et     H        H    cPr                                               7.057   nPr    H        H    cPr                                               7.058   Me     Me       H    cPr                                               7.059   Et     Me       H    cPr                                               7.060   nPr    Me       H    cPr                                               7.061   Me     Me       Me   cPr                                               7.062   Et     Me       Me   cPr                                               7.063   nPr    Me       Me   cPr                                               7.064   Me     H        H    CH.sub.2 OMe                                                                              oil                                    7.065   Et     H        H    CH.sub.2 OMe                                      7.066   nPr    H        H    CH.sub.2 OMe                                      7.067   Me     Me       H    CH.sub.2 OMe                                      7.068   Et     Me       H    CH.sub.2 OMe                                      7.069   nPr    Me       H    CH.sub.2 OMe                                      7.070   Me     Me       Me   CH.sub.2 OMe                                      7.071   Et     Me       Me   CH.sub.2 OMe                                      7.072   nPr    Me       Me   CH.sub.2 OMe                                      7.073   Me     H        H    CH.sub.2 OEt                                                                              oil                                    7.074   Et     H        H    CH.sub.2 OEt                                      7.075   nPr    H        H    CH.sub.2 OEt                                      7.076   Me     Me       H    CH.sub.2 OEt                                      7.077   Et     Me       H    CH.sub.2 OEt                                      7.078   nPr    Me       H    CH.sub.2 OEt                                      7.079   Me     Me       Me   CH.sub.2 OEt                                      7.080   Et     Me       Me   CH.sub.2 OEt                                      7.081   nPr    Me       Me   CH.sub.2 OEt                                      7.082   Me     H        H    CH.sub.2 OnPr                                     7.083   Et     H        H    CH.sub.2 OnPr                                     7.084   nPr    H        H    CH.sub.2 OnPr                                     7.085   Me     Me       H    CH.sub.2 OnPr                                     7.086   Et     Me       H    CH.sub.2 OnPr                                     7.087   nPr    Me       H    CH.sub.2 OnPr                                     7.088   Me     Me       Me   CH.sub.2 OnPr                                     7.089   Et     Me       Me   CH.sub.2 OnPr                                     7.090   nPr    Me       Me   CH.sub.2 OnPr                                     7.091   Me     H        H    CH.sub.2 SMe                                      7.092   Et     H        H    CH.sub.2 SMe                                      7.093   nPr    H        H    CH.sub.2 SMe                                      7.094   Me     Me       H    CH.sub.2 SMe                                      7.095   Et     Me       H    CH.sub.2 SMe                                      7.096   nPr    Me       H    CH.sub.2 SMe                                      7.097   Me     Me       Me   CH.sub.2 SMe                                      7.098   Et     Me       Me   CH.sub.2 SMe                                      7.099   nPr    Me       Me   CH.sub.2 SMe                                      7.100   Me     H        H    CH.sub.2 SEt                                      7.101   Et     H        H    CH.sub.2 SEt                                      7.102   nPr    H        H    CH.sub.2 SEt                                      7.103   Me     Me       H    CH.sub.2 SEt                                      7.104   Et     Me       H    CH.sub.2 SEt                                      7.105   nPr    Me       H    CH.sub.2 SEt                                      7.106   Me     Me       Me   CH.sub.2 SEt                                      7.107   Et     Me       Me   CH.sub.2 SEt                                      7.108   nPr    Me       Me   CH.sub.2 SEt                                      7.109   Me     H        H    CH.sub.2 SnPr                                     7.110   Et     H        H    CH.sub.2 SnPr                                     7.111   nPr    H        H    CH.sub.2 SnPr                                     7.112   Me     Me       H    CH.sub.2 SnPr                                     7.113   Et     Me       H    CH.sub.2 SnPr                                     7.114   nPr    Me       H    CH.sub.2 SnPr                                     7.115   Me     Me       Me   CH.sub.2 SnPr                                     7.116   Et     Me       Me   CH.sub.2 SnPr                                     7.117   nPr    Me       Me   CH.sub.2 SnPr                                     7.118   Me     H        H    CH.sub.2 OCOMe                                                                            147-148°                        ______________________________________                                    

EXAMPLE P30 Acetic acid 1-cyclopropyl-2-(5-methoxy-2-oxo- 1,3,4!thiadiazol-3-yl)-ethylidene!-hydrazide (Compound 8.055a in Table 8a)

16 g of acetyl hydrazide are added to a solution of 39.5 g of 3-(2-cyclopropyl-2-oxo-ethyl)-5-methoxy-3H- 1,3,4!thiadiazol-2-one (Comp. 7.055) in 350 ml of methanol and the mixture is then stirred at 55° for 16 hours. The reaction mixture is concentrated by evaporation, and the residue is stirred with ether/diisopropyl ether and filtered with suction to yield 40.5 g of crystals of the title compound having a melting point of 100°-102°.

EXAMPLE P31

Acetic acid 2-(5-methoxy-2-oxo- 1,3,4!thiadiazol-3-yl)-1-methylethylidene!-hydrazide (Compound 8.001a in Table 8a)

7.4 g of acetyl hydrazide are added to a solution of 18.8 g of 5-methoxy-3-(2-oxo-propyl)-3H- 1,3,4!thiadiazol-2-one (Comp. 7.001) in 150 ml of methanol and the mixture is then stirred at 55° for 2 hours. The reaction mixture is concentrated by evaporation and the residue is stirred with isopropanol and filtered with suction to yield 21.5 g of crystals of the title compound having a melting point of 151°-153°.

EXAMPLE P32 Acetic acid 1-ethoxymethyl-2-(5-methoxy-2-oxo- 1,3,4!thiadiazol-3-yl)-ethylidene!-hydrazide (Compound 8.073a in Table 8a)

12.6 g of acetyl hydrazide and 1 ml of acetic acid are added to a solution of 35.5 g of 3-(3-ethoxy-2-oxo-propyl)-5-methoxy-3H- 1,3,4!thiadiazol-2-one (Comp. 7.073) in 400 ml of methanol and 200 ml of tetrahydrofuran and the mixture is then stirred at 60° for 2 hours. The reaction mixture is concentrated by evaporation and the residue is stirred with isopropanol and filtered with suction to yield 31.5 g of crystals of the title compound having a melting point of 97°-98°.

EXAMPLE P33

The other compounds listed in Table 8a can also be prepared in a manner analogous to that described in Examples P30 to P32.

                  TABLE 8a                                                         ______________________________________                                          ##STR27##                                                                     Comp.   R      R.sub.1  R.sub.2                                                                             R.sub.6    m.p.                                   ______________________________________                                         8.001.a Me     H        H    Me         151-153°                        8.002.a Et     H        H    Me                                                8.003.a nPr    H        H    Me                                                8.004.a Me     Me       H    Me                                                8.005.a Et     Me       H    Me         115-117°                        8.006.a nPr    Me       H    Me                                                8.007.a Me     Me       Me   Me                                                8.008.a Et     Me       Me   Me                                                8.009.a nPr    Me       Me   Me                                                8.010.a Me     H        H    Et                                                8.011.a Et     H        H    Et                                                8.012.a nPr    H        H    Et                                                8.013.a Me     Me       H    Et                                                8.014.a Et     Me       H    Et                                                8.015.a nPr    Me       H    Et                                                8.016.a Me     Me       Me   Et                                                8.017.a Et     Me       Me   Et                                                8.018.a nPr    Me       Me   Et                                                8.019.a Me     H        H    nPr                                               8.020.a Et     H        H    nPr                                               8.021.a nPr    H        H    nPr                                               8.022.a Me     Me       H    nPr                                               8.023.a Et     Me       H    nPr                                               8.024.a nPr    Me       H    nPr                                               8.025.a Me     Me       Me   nPr                                               8.026.a Et     Me       Me   nPr                                               8.027.a nPr    Me       Me   nPr                                               8.028.a Me     H        H    nBu        98-99°                          8.029.a Et     H        H    nBu                                               8.030.a nPr    H        H    nBu                                               8.031.a Me     Me       H    nBu                                               8.032.a Et     Me       H    nBu                                               8.033.a nPr    Me       H    nBu                                               8.034.a Me     Me       Me   nBu                                               8.035.a Et     Me       Me   nBu                                               8.036.a nPr    Me       Me   nBu                                               8.037.a Me     H        H    iPr                                               8.038.a Et     H        H    iPr                                               8.039.a nPr    H        H    iPr                                               8.040.a Me     Me       H    iPr                                               8.041.a Et     Me       H    iPr                                               8.042.a nPr    Me       H    iPr                                               8.043.a Me     Me       Me   iPr                                               8.044.a Et     Me       Me   iPr                                               8.045.a nPr    Me       Me   iPr                                               8.046.a Me     H        H    tBu        119-120°                        8.047.a Et     H        H    tBu                                               8.048.a nPr    H        H    tBu                                               8.049.a Me     Me       H    tBu                                               8.050.a Et     Me       H    tBu                                               8.051.a nPr    Me       H    tBu                                               8.052.a Me     Me       Me   tBu                                               8.053.a Et     Me       Me   tBu                                               8.054.a nPr    Me       Me   tBu                                               8.055.a Me     H        H    cPr        100-102°                        8.056.a Et     H        H    cPr                                               8.057.a nPr    H        H    cPr                                               8.058.a Me     Me       H    cPr                                               8.059.a Et     Me       H    cPr                                               8.060.a nPr    Me       H    cPr                                               8.061.a Me     Me       Me   cPr                                               8.062.a Et     Me       Me   cPr                                               8.063.a nPr    Me       Me   cPr                                               8.064.a Me     H        H    CH.sub.2 OMe                                                                              102-104°                        8.065.a Et     H        H    CH.sub.2 OMe                                      8.066.a nPr    H        H    CH.sub.2 OMe                                      8.067.a Me     Me       H    CH.sub.2 OMe                                      8.068.a Et     Me       H    CH.sub.2 OMe                                      8.069.a nPr    Me       H    CH.sub.2 OMe                                      8.070.a Me     Me       Me   CH.sub.2 OMe                                      8.071.a Et     Me       Me   CH.sub.2 OMe                                      8.072.a nPr    Me       Me   CH.sub.2 OMe                                      8.073.a Me     H        H    CH.sub.2 OEt                                                                              97-98°                          8.074.a Et     H        H    CH.sub.2 OEt                                      8.075.a nPr    H        H    CH.sub.2 OEt                                      8.076.a Me     Me       H    CH.sub.2 OEt                                      8.077.a Et     Me       H    CH.sub.2 OEt                                      8.078.a nPr    Me       H    CH.sub.2 OEt                                      8.079.a Me     Me       Me   CH.sub.2 OEt                                      8.080.a Et     Me       Me   CH.sub.2 OEt                                      8.081.a nPr    Me       Me   CH.sub.2 OEt                                      8.082.a Me     H        H    CH.sub.2 OnPr                                     8.083.a Et     H        H    CH.sub.2 OnPr                                     8.084.a nPr    H        H    CH.sub.2 OnPr                                     8.085.a Me     Me       H    CH.sub.2 OnPr                                     8.086.a Et     Me       H    CH.sub.2 OnPr                                     8.087.a nPr    Me       H    CH.sub.2 OnPr                                     8.088.a Me     Me       Me   CH.sub.2 OnPr                                     8.089.a Et     Me       Me   CH.sub.2 OnPr                                     8.090.a nPr    Me       Me   CH.sub.2 OnPr                                     8.091.a Me     H        H    CH.sub.2 SMe                                      8.092.a Et     H        H    CH.sub.2 SMe                                      8.093.a nPr    H        H    CH.sub.2 SMe                                      8.094.a Me     Me       H    CH.sub.2 SMe                                      8.095.a Et     Me       H    CH.sub.2 SMe                                      8.096.a nPr    Me       H    CH.sub.2 SMe                                      8.097.a Me     Me       Me   CH.sub.2 SMe                                      8.098.a Et     Me       Me   CH.sub.2 SMe                                      8.099.a nPr    Me       Me   CH.sub.2 SMe                                      8.100.a Me     H        H    CH.sub.2 SEt                                      8.101.a Et     H        H    CH.sub.2 SEt                                      8.102.a nPr    H        H    CH.sub.2 SEt                                      8.103.a Me     Me       H    CH.sub.2 SEt                                      8.104.a Et     Me       H    CH.sub.2 SEt                                      8.105.a nPr    Me       H    CH.sub.2 SEt                                      8.106.a Me     Me       Me   CH.sub.2 SEt                                      8.107.a Et     Me       Me   CH.sub.2 SEt                                      8.108.a nPr    Me       Me   CH.sub.2 SEt                                      8.109.a Me     H        H    CH.sub.2 SnPr                                     8.110.a Et     H        H    CH.sub.2 SnPr                                     8.111.a nPr    H        H    CH.sub.2 SnPr                                     8.112.a Me     Me       H    CH.sub.2 SnPr                                     8.113.a Et     Me       H    CH.sub.2 SnPr                                     8.114.a nPr    Me       H    CH.sub.2 SnPr                                     8.115.a Me     Me       Me   CH.sub.2 SnPr                                     8.116.a Et     Me       Me   CH.sub.2 SnPr                                     8.117.a nPr    Me       Me   CH.sub.2 SnPr                                     ______________________________________                                    

EXAMPLE P34 N'- 2-(5-Methoxy-2-oxo- 1,3,4!thiadiazol-3-yl)-1-methyl-ethylidene!-hydrazinecarboxylic acid methyl ester (Compound 8.001 b in Table 8b)

9.1 g of methyl carbazate are added to a solution of 18.8 g of 5-methoxy-3-(2-oxo-propyl)-3H- 1,3,4!thiadiazol-2-one (Comp. 7.001) in 150 ml of methanol and the mixture is then stirred at room temperature for 36 hours. The reaction mixture is concentrated by evaporation and the residue is stirred with isopropanol and filtered with suction to yield 20.5 g of crystals of the title compound having a melting point of 142°-143°.

EXAMPLE P35

The other compounds listed in Table 8b can also be prepared in a manner analogous to that described in Example P34.

                  TABLE 8b                                                         ______________________________________                                          ##STR28##                                                                     Comp.    R       R.sub.1 R.sub.2                                                                              R.sub.6  m.p.                                   ______________________________________                                         8.001.b  Me      H       H     Me       142-143°                        8.002.b  Et      H       H     Me                                              8.003.b  nPr     H       H     Me                                              8.004.b  Me      Me      H     Me                                              8.005.b  Et      Me      H     Me                                              8.006.b  nPr     Me      H     Me                                              8.007.b  Me      Me      Me    Me                                              8.008.b  Et      Me      Me    Me                                              8.009.b  nPr     Me      Me    Me                                              8.010.b  Me      H       H     Et                                              8.011.b  Et      H       H     Et                                              8.012.b  nPr     H       H     Et                                              8.013.b  Me      Me      H     Et                                              8.014.b  Et      Me      H     Et                                              8.015.b  nPr     Me      H     Et                                              8.016.b  Me      Me      Me    Et                                              8.017.b  Et      Me      Me    Et                                              8.018.b  nPr     Me      Me    Et                                              8.019.b  Me      H       H     nPr                                             8.020.b  Et      H       H     nPr                                             8.021.b  nPr     H       H     nPr                                             8.022.b  Me      Me      H     nPr                                             8.023.b  Et      Me      H     nPr                                             8.024.b  nPr     Me      H     nPr                                             8.025.b  Me      Me      Me    nPr                                             8.026.b  Et      Me      Me    nPr                                             8.027.b  nPr     Me      Me    nPr                                             8.028.b  Me      H       H     nBu                                             8.029.b  Et      H       H     nBu                                             8.030.b  nPr     H       H     nBu                                             8.031.b  Me      Me      H     nBu                                             8.032.b  Et      Me      H     nBu                                             8.033.b  nPr     Me      H     nBu                                             8.034.b  Me      Me      Me    nBu                                             8.035.b  Et      Me      Me    nBu                                             8.036.b  nPr     Me      Me    nBu                                             8.037.b  Me      H       H     iPr                                             8.038.b  Et      H       H     iPr                                             8.039.b  nPr     H       H     iPr                                             8.040.b  Me      Me      H     iPr                                             8.041.b  Et      Me      H     iPr                                             8.042.b  nPr     Me      H     iPr                                             8.043.b  Me      Me      Me    iPr                                             8.044.b  Et      Me      Me    iPr                                             8.045.b  nPr     Me      Me    iPr                                             8.046.b  Me      H       H     tBu                                             8.047.b  Et      H       H     tBu                                             8.048.b  nPr     H       H     tBu                                             8.049.b  Me      Me      H     tBu                                             8.050.b  Et      Me      H     tBu                                             8.051.b  nPr     Me      H     tBu                                             8.052.b  Me      Me      Me    tBu                                             8.053.b  Et      Me      Me    tBu                                             8.054.b  nPr     Me      Me    tBu                                             8.055.b  Me      H       H     cPr                                             8.056.b  Et      H       H     cPr                                             8.057.b  nPr     H       H     cPr                                             8.058.b  Me      Me      H     cPr                                             8.059.b  Et      Me      H     cPr                                             8.060.b  nPr     Me      H     cPr                                             8.061.b  Me      Me      Me    cPr                                             8.062.b  Et      Me      Me    cPr                                             8.063.b  nPr     Me      Me    cPr                                             8.064.b  Me      H       H     CH.sub.2 OMe                                    8.065.b  Et      H       H     CH.sub.2 OMe                                    8.066.b  nPr     H       H     CH.sub.2 OMe                                    8.067.b  Me      Me      H     CH.sub.2 OMe                                    8.068.b  Et      Me      H     CH.sub.2 OMe                                    8.069.b  nPr     Me      H     CH.sub.2 OMe                                    8.070.b  Me      Me      Me    CH.sub.2 OMe                                    8.071.b  Et      Me      Me    CH.sub.2 OMe                                    8.072.b  nPr     Me      Me    CH.sub.2 OMe                                    8.073.b  Me      H       H     CH.sub.2 OEt                                    8.074.b  Et      H       H     CH.sub.2 OEt                                    8.075.b  nPr     H       H     CH.sub.2 OEt                                    8.076.b  Me      Me      H     CH.sub.2 OEt                                    8.077.b  Et      Me      H     CH.sub.2 OEt                                    8.078.b  nPr     Me      H     CH.sub.2 OEt                                    8.079.b  Me      Me      Me    CH.sub.2 OEt                                    8.080.b  Et      Me      Me    CH.sub.2 OEt                                    8.081.b  nPr     Me      Me    CH.sub.2 OEt                                    8.082.b  Me      H       H     CH.sub.2 OnPr                                   8.083.b  Et      H       H     CH.sub.2 OnPr                                   8.084.b  nPr     H       H     CH.sub.2 OnPr                                   8.085.b  Me      Me      H     CH.sub.2 OnPr                                   8.086.b  Et      Me      H     CH.sub.2 OnPr                                   8.087.b  nPr     Me      H     CH.sub.2 OnPr                                   8.088.b  Me      Me      Me    CH.sub.2 OnPr                                   8.089.b  Et      Me      Me    CH.sub.2 OnPr                                   8.090.b  nPr     Me      Me    CH.sub.2 OnPr                                   8.091.b  Me      H       H     CH.sub.2 SMe                                    8.092.b  Et      H       H     CH.sub.2 SMe                                    8.093.b  nPr     H       H     CH.sub.2 SMe                                    8.094.b  Me      Me      H     CH.sub.2 SMe                                    8.095.b  Et      Me      H     CH.sub.2 SMe                                    8.096.b  nPr     Me      H     CH.sub.2 SMe                                    8.097.b  Me      Me      Me    CH.sub.2 SMe                                    8.098.b  Et      Me      Me    CH.sub.2 SMe                                    8.099.b  nPr     Me      Me    CH.sub.2 SMe                                    8.100.b  Me      H       H     CH.sub.2 SEt                                    8.101.b  Et      H       H     CH.sub.2 SEt                                    8.102.b  nPr     H       H     CH.sub.2 SEt                                    8.103.b  Me      Me      H     CH.sub.2 SEt                                    8.104.b  Et      Me      H     CH.sub.2 SEt                                    8.105.b  nPr     Me      H     CH.sub.2 SEt                                    8.106.b  Me      Me      Me    CH.sub.2 SEt                                    8.107.b  Et      Me      Me    CH.sub.2 SEt                                    8.108.b  nPr     Me      Me    CH.sub.2 SEt                                    8.109.b  Me      H       H     CH.sub.2 SnPr                                   8.110.b  Et      H       H     CH.sub.2 SnPr                                   8.111.b  nPr     H       H     CH.sub.2 SnPr                                   8.112.b  Me      Me      H     CH.sub.2 SnPr                                   8.113.b  Et      Me      H     CH.sub.2 SnPr                                   8.114.b  nPr     Me      H     CH.sub.2 SnPr                                   8.115.b  Me      Me      Me    CH.sub.2 SnPr                                   8.116.b  Et      Me      Me    CH.sub.2 SnPr                                   8.117.b  nPr     Me      Me    CH.sub.2 SnPr                                   ______________________________________                                    

EXAMPLE P36 (6-Methyl-3-oxo-2,5-dihydro-3H- 1,3,4!triazin-4-yl)-thiocarbamic acid O-methyl ester (Compound 9.001 in Table 9)

14.5 ml of a 30% solution of sodium methoxide are added dropwise to a suspension of 18.7 g of acetic acid 2-(5-methoxy-2-oxo- 1,3,4!thiadiazol-3-yl)-1-methylethylidene!-hydrazide (Comp. 8.001a) in 200 ml of methanol and the mixture is then stirred at room temperature for 3 hours. The mixture is then concentrated by evaporation, 250 ml of water are added, the mixture is rendered slightly acidic by the addition of hydrochloric acid and then extracted three times with 100 ml of ethyl acetate. The organic phase is dried using magnesium sulfate and concentrated by evaporation to yield 9 g of crystals of the title compound having a melting point of 185°-187°.

EXAMPLE P37 (6-Ethoxymethyl-3-oxo-2,5-dihydro-3H- 1,3,4!triazin-4-yl)-thiocarbamic acid O-methyl ester (Compound 9.073 in Table 9)

25 ml of a 30% solution of sodium methoxide are added dropwise to a suspension of 29.9 g of acetic acid 1-ethoxymethyl-2-(5-methoxy-2-oxo- 1,3,4!thiadiazol-3-yl)-ethylidene!-hydrazide (Comp. 8.073a) in 250 ml of methanol and the mixture is then stirred at 60° for 2 hours. The mixture is then concentrated by evaporation, 250 ml of water are added, the mixture is adjusted to pH 4.5 using hydrochloric acid and then extracted three times with 100 ml of ethyl acetate. The organic phase is dried using magnesium sulfate and concentrated by evaporation to yield 20.6 g of crystals of the title compound having a melting point of 132°-134°.

EXAMPLE P38 (6-Cyclopropyl-3-oxo-2,5-dihydro-3H- 1,3,4!triazin-4-yl)-thiocarbamic acid O-methyl ester (Compound 9.055 in Table 9)

33 ml of a 30% solution of sodium methoxide are added dropwise at 50° to a solution of 39.5 g of acetic acid 1-cyclopropyl-2-(5-methoxy-2-oxo- 1,3,4!thiadiazol-3-yl)-ethylidene!-hydrazide (Comp. 8.055a) in 500 ml of methanol and the mixture is then stirred at 60° for 4 hours. The mixture is then concentrated by evaporation, 400 ml of water are added and the mixture is adjusted to pH 2 using hydrochloric acid, whereupon the product precipitates in the form of crystals. The mixture is dried overnight at 60° in vacuo, to yield 24.6 g of crystals of the title compound having a melting point of 163°-166°.

EXAMPLE P39

The compounds listed in Table 8b can also be prepared in a manner analogous to that described in Examples P36 to P38.

                  TABLE 9                                                          ______________________________________                                          ##STR29##                                                                     Comp.    R       R.sub.1 R.sub.2                                                                              R.sub.6                                                                               m.p.                                     ______________________________________                                         9.001    Me      H       H     Me     185-187°                          9.002    Et      H       H     Me                                              9.003    nPr     H       H     Me                                              9.004    Me      Me      H     Me     202-203°                          9.005    Et      Me      H     Me                                              9.006    nPr     Me      H     Me                                              9.007    Me      Me      Me    Me                                              9.008    Et      Me      Me    Me                                              9.009    nPr     Me      Me    Me                                              9.010    Me      H       H     Et                                              9.011    Et      H       H     Et                                              9.012    nPr     H       H     Et                                              9.013    Me      Me      H     Et                                              9.014    Et      Me      H     Et                                              9.015    nPr     Me      H     Et                                              9.016    Me      Me      Me    Et                                              9.017    Et      Me      Me    Et                                              9.018    nPr     Me      Me    Et                                              9.019    Me      H       H     nPr                                             9.020    Et      H       H     nPr                                             9.021    nPr     H       H     nPr                                             9.022    Me      Me      H     nPr                                             9.023    Et      Me      H     nPr                                             9.024    nPr     Me      H     nPr                                             9.025    Me      Me      Me    nPr                                             9.026    Et      Me      Me    nPr                                             9.027    nPr     Me      Me    nPr                                             9.028    Me      H       H     nBu                                             9.029    Et      H       H     nBu                                             9.030    nPr     H       H     nBu                                             9.031    Me      Me      H     nBu                                             9.032    Et      Me      H     nBu                                             9.033    nPr     Me      H     nBu                                             9.034    Me      Me      Me    nBu                                             9.035    Et      Me      Me    nBu                                             9.036    nPr     Me      Me    nBu                                             9.037    Me      H       H     iPr                                             9.038    Et      H       H     iPr                                             9.039    nPr     H       H     iPr                                             9.040    Me      Me      H     iPr                                             9.041    Et      Me      H     iPr                                             9.042    nPr     Me      H     iPr                                             9.043    Me      Me      Me    iPr                                             9.044    Et      Me      Me    iPr                                             9.045    nPr     Me      Me    iPr                                             9.046    Me      H       H     tBu    203-205°                          9.047    Et      H       H     tBu                                             9.048    nPr     H       H     tBu                                             9.049    Me      Me      H     tBu                                             9.050    Et      Me      H     tBu                                             9.051    nPr     Me      H     tBu                                             9.052    Me      Me      Me    tBu                                             9.053    Et      Me      Me    tBu                                             9.054    nPr     Me      Me    tBu                                             9.055    Me      H       H     cPr    163-166°                          9.056    Et      H       H     cPr                                             9.057    nPr     H       H     cPr                                             9.058    Me      Me      H     cPr                                             9.059    Et      Me      H     cPr                                             9.060    nPr     Me      H     cPr                                             9.061    Me      Me      Me    cPr                                             9.062    Et      Me      Me    cPr                                             9.063    nPr     Me      Me    cPr                                             9.064    Me      H       H     CH.sub.2 OMe                                                                          165-167°                          9.065    Et      H       H     CH.sub.2 OMe                                    9.066    nPr     H       H     CH.sub.2 OMe                                    9.067    Me      Me      H     CH.sub.2 OMe                                    9.068    Et      Me      H     CH.sub.2 OMe                                    9.069    nPr     Me      H     CH.sub.2 OMe                                    9.070    Me      Me      Me    CH.sub.2 OMe                                    9.071    Et      Me      Me    CH.sub.2 OMe                                    9.072    nPr     Me      Me    CH.sub.2 OMe                                    9.073    Me      H       H     CH.sub.2 OEt                                                                          132-134°                          9.074    Et      H       H     CH.sub.2 OEt                                    9.075    nPr     H       H     CH.sub.2 OEt                                    9.076    Me      Me      H     CH.sub.2 OEt                                    9.077    Et      Me      H     CH.sub.2 OEt                                    9.078    nPr     Me      H     CH.sub.2 OEt                                    9.079    Me      Me      Me    CH.sub.2 OEt                                    9.080    Et      Me      Me    CH.sub.2 OEt                                    9.081    nPr     Me      Me    CH.sub.2 OEt                                    9.082    Me      H       H     CH.sub.2 OnPr                                   9.083    Et      H       H     CH.sub.2 OnPr                                   9.084    nPr     H       H     CH.sub.2 OnPr                                   9.085    Me      Me      H     CH.sub.2 OnPr                                   9.086    Et      Me      H     CH.sub.2 OnPr                                   9.087    nPr     Me      H     CH.sub.2 OnPr                                   9.088    Me      Me      Me    CH.sub.2 OnPr                                   9.089    Et      Me      Me    CH.sub.2 OnPr                                   9.090    nPr     Me      Me    CH.sub.2 OnPr                                   9.091    Me      H       H     CH.sub.2 SMe                                    9.092    Et      H       H     CH.sub.2 SMe                                    9.093    nPr     H       H     CH.sub.2 SMe                                    9.094    Me      Me      H     CH.sub.2 SMe                                    9.095    Et      Me      H     CH.sub.2 SMe                                    9.096    nPr     Me      H     CH.sub.2 SMe                                    9.097    Me      Me      Me    CH.sub.2 SMe                                    9.098    Et      Me      Me    CH.sub.2 SMe                                    9.099    nPr     Me      Me    CH.sub.2 SMe                                    9.100    Me      H       H     CH.sub.2 SEt                                    9.101    Et      H       H     CH.sub.2 SEt                                    9.102    nPr     H       H     CH.sub.2 SEt                                    9.103    Me      Me      H     CH.sub.2 SEt                                    9.104    Et      Me      H     CH.sub.2 SEt                                    9.105    nPr     Me      H     CH.sub.2 SEt                                    9.106    Me      Me      Me    CH.sub.2 SEt                                    9.107    Et      Me      Me    CH.sub.2 SEt                                    9.108    nPr     Me      Me    CH.sub.2 SEt                                    9.109    Me      H       H     CH.sub.2 SnPr                                   9.110    Et      H       H     CH.sub.2 SnPr                                   9.111    nPr     H       H     CH.sub.2 SnPr                                   9.112    Me      Me      H     CH.sub.2 SnPr                                   9.113    Et      Me      H     CH.sub.2 SnPr                                   9.114    nPr     Me      H     CH.sub.2 SnPr                                   9.115    Me      Me      Me    CH.sub.2 SnPr                                   9.116    Et      Me      Me    CH.sub.2 SnPr                                   9.117    nPr     Me      Me    CH.sub.2 SnPr                                   9.118    Me      H       H     CH.sub.2 OH                                                                           165-170°                          ______________________________________                                    

Formulation Examples (throughout, percentages are by weight)

                  EXAMPLE F1                                                       ______________________________________                                         Emulsifiable concentrates                                                                         a)       b)     c)                                          ______________________________________                                         active ingredient  25%      40%    50%                                         calcium dodecylbenzenesulfonate                                                                    5%       8%     6%                                         castor oil polyethylene glycol                                                                     5%      --     --                                          ether (36 mol of ethylene oxide)                                               tributylphenol polyethylene glycol                                                                --       12%     4%                                         ether (30 mol of ethylene oxide)                                               cyclohexanone      --       15%    20%                                         xylene mixture     65%      25%    20%                                         ______________________________________                                    

The finely ground active ingredient is mixed with the adjuvants, giving an emulsifiable concentrate from which emulsions of any desired concentration can be prepared by dilution with water.

                  EXAMPLE F2                                                       ______________________________________                                         Solutions        a)      b)      c)    d)                                      ______________________________________                                         active ingredient                                                                               80%     10%     5%    95%                                     ethylene glycol monomethyl                                                                      20%     --      --    --                                      ether                                                                          polyethylene glycol                                                                             --      70%     --    --                                      (mol. wt. 400)                                                                 N-methylpyrrolid-2-one                                                                          --      20%     --    --                                      epoxidised coconut oil                                                                          --      --      1%     5%                                     petroleum fraction                                                                              --      --      94%   --                                      (boiling range 160-190° C.)                                             ______________________________________                                    

The finely ground active ingredient is mixed with the adjuvants, giving a solution that is suitable for application in the form of microdrops.

                  EXAMPLE F3                                                       ______________________________________                                         Granules         a)     b)       c)   d)                                       ______________________________________                                         active ingredient                                                                               5%     10%       8%  21%                                      kaolin           94%    --       79%  54%                                      highly dispersed silicic acid                                                                   1%     --       13%   7%                                      attapulgite      --     90%      --   18%                                      ______________________________________                                    

The active ingredient is dissolved in dichloromethane, the solution is sprayed onto the carrier mixture, and the solvent is evaporated off in vacuo.

                  EXAMPLE F4                                                       ______________________________________                                         Dusts                a)     b)                                                 ______________________________________                                         active ingredient    2%     5%                                                 highly dispersed silicic acid                                                                       1%     5%                                                 talcum               97%    --                                                 kaolin               --     90%                                                ______________________________________                                    

Ready-for-use dusts are obtained by mixing the active ingredient with the carriers.

                  EXAMPLE F5                                                       ______________________________________                                         Wettable powders a)         b)     c)                                          ______________________________________                                         active ingredient                                                                               25%        50%    75%                                         sodium lignosulfonate                                                                           5%          5%    --                                          sodium lauryl sulfate                                                                           3%         --      5%                                         sodium diisobutylnaphthalene-                                                                   --          6%    10%                                         sulfonate                                                                      octylphenol polyethylene                                                                        --          2%    --                                          glycol ether (7-8 mol of                                                       ethylene oxide)                                                                highly dispersed silicic acid                                                                   5%         10%    10%                                         kaolin           62%        27%    --                                          ______________________________________                                    

The active ingredient is mixed with the adjuvants and the mixture is ground in a suitable mill, affording wettable powders which can be diluted with water to give suspensions of any desired concentration.

                  EXAMPLE F6                                                       ______________________________________                                         Emulsifiable concentrate                                                       ______________________________________                                         active ingredient     10%                                                      octylphenol polyethylene glycol ether                                                                 3%                                                      (4-5 mol of ethylene oxide)                                                    calcium dodecylbenzenesulfonate                                                                       3%                                                      castor oil polyethylene glycol ether                                           (36 mol of ethylene oxide)                                                                            4%                                                      cyclohexanone         30%                                                      xylene mixture        50%                                                      ______________________________________                                    

The finely ground active ingredient is mixed with the adjuvants, giving an emulsifiable concentrate from which emulsions of any desired concentration can be prepared by dilution with water.

                  EXAMPLE F7                                                       ______________________________________                                         Dusts              a)     b)                                                   ______________________________________                                         active ingredient   5%     8%                                                  talcum             95%    --                                                   kaolin             --     92%                                                  ______________________________________                                    

Ready-for-use dusts are obtained by mixing the active ingredient with the carrier and grinding the mixture in a suitable mill.

                  EXAMPLE F8                                                       ______________________________________                                         Extruder granules                                                              ______________________________________                                         active ingredient  10%                                                         sodium lignosulfonate                                                                              2%                                                         carboxymethylcellulose                                                                             1%                                                         kaolin             87%                                                         ______________________________________                                    

The active ingredient is mixed with the adjuvants, and the mixture is ground, moistened with water, extruded and granulated, and the granules are then dried in a stream of air.

                  EXAMPLE F9                                                       ______________________________________                                         Coated granules                                                                ______________________________________                                         active ingredient    3%                                                        polyethylene glycol (mol. wt. 200)                                                                  3%                                                        kaolin               94%                                                       ______________________________________                                    

The finely ground active ingredient is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol, affording non-dusty coated granules.

                  EXAMPLE F10                                                      ______________________________________                                         Suspension concentrate                                                         active ingredient     40%                                                      ethylene glycol       10%                                                      nonylphenol polyethylene glycol ether                                                                 6%                                                      (15 mol of ethylene oxide)                                                     sodium lignosulfonate 10%                                                      carboxymethylcellulose                                                                                1%                                                      aqueous formaldehyde solution (37%)                                                                    0.2%                                                   aqueous silicone oil emulsion (75%)                                                                    0.8%                                                   water                 32%                                                      ______________________________________                                    

The finely ground active ingredient is mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired concentration can be obtained by dilution with water.

BIOLOGICAL EXAMPLES Example B1 Action against Aphis craccivora

Pea seedlings are infested with Aphis craccivora and then sprayed with a spray mixture comprising 400 ppm of test compound, and incubated at 20° C. Evaluation is made 3 and 6 days later. The percentage reduction in the population (% activity) is determined by comparing the number of dead aphids on the treated plants with that on untreated plants.

Compounds of Tables 1 and 1b exhibit good activity in this test. In particular, Compound No. 1.072 is more than 80% effective.

Example B2 Action against Nilaparvata Luzens

Rice plants are sprayed with an aqueous emulsion comprising 400 ppm of test compound. After the spray coating has dried, the rice plants are populated with plant hopper larvae in the 2nd and 3rd stages. Evaluation is made 21 days later. The percentage reduction in the population (% activity) is determined by comparing the number of surviving plant hoppers on the treated plants with that on untreated plants.

Compounds of Tables 1 and 1b exhibit good activity in this test In particular, Compound No. 1.072 is more than 80% effective.

Example B3 Action against Nilaparvata Lugens (Systemic)

Pots containing rice plants are stood in an aqueous emulsion comprising 10 ppm of test compound. The plants are then populated with larvae in the 2nd and 3rd stages. Evaluation is made 6 days later. The percentage reduction in the population (% activity) is determined by comparing the number of plant hoppers on the treated plants with that on untreated plants.

Compounds of Tables 1 and 1b exhibit good activity in this test. In particular, Compound No. 1.072 is more than 80% effective. 

What is claimed is:
 1. A compound of formula ##STR30## in free or salt form, or a tautomer thereof, wherein R₁, R₂ and R₆ are each independently of the other H, halogen, C₁ -C₅ alkyl, C₁ -C₅ alkoxy, C₁ -C₃ alkoxy-C₁ -C₅ alkyl, hydroxy-C₁ -C₅ alkyl, C₁ -C₅ alkoxycarbonyl, C₁ -C₅ alkylthio; C₁ -C₅ alkyl substituted by from 1 to 3 substituents selected from the group consisting of halogen, hydroxy, C₁ -C₃ alkoxy, C₁ -C₃ alkoxycarbonyl and C₁ -C₃ alkylthio; C₃ -C₆ cycloalkyl or C₃ -C₆ cycloalkyl substituted by from 1 to 3 substituents selected from the group consisting of halogen and C₁ -C₃ alkyl;R₁ and R₂ when taken together are ═O, ═NH or ═S and R"' and R"" are each independently of the other C₁ -C₆ alkyl.
 2. A process for the preparation of a compound according to claim 1, in free form or in salt form, which process comprisesreacting a compound of formula ##STR31## with a compound of the formula NH₂ NHCOR"". 